How to develop a winning sales strategy

37 min read

Kent Holland

Kent Holland leads Copper’s Global Sales Organization. Prior to Copper, Kent was a business development leader at Box, helped drive new product launches and sales strategy at LinkedIn, and started his career in the strategy and operations consulting practice at Deloitte.

Kent was featured on our Limitless webinar series on February 11, 2020 at 11 AM EST. He had some really great insights to be shared on developing winning sales strategies.

Key takeaways from the webinar:

  • Designing a sales organization (and GTM motion) to optimize for efficiency and customer experience
  • Personalization at scale vs. volume outreach
  • Identifying and focusing on the right (consolidated) set of KPIs
  • Driving improvements in MQL: Win rate
  • Building an engaged and effective startup sales team

Watch the complete webinar:

Webinar Transcription:

Host: Vivek

Speaker: Kent Holland

Vivek: Hello, everyone. Welcome to another episode of Limitless Webinar Series where we bring you the top seeds leaders in this industry to share their experience, strategy, best practices and most importantly, actionable inputs that you can readily implement in your jobs. We have an amazing guest with us today, we have Kent Holland, the vice president of sales at Copper CRM.

Hi, Kent. Good to have you here. Would you like to say hello to us?

Kent: Vivek and hey, everyone, thanks for joining today.

Excited to chat a little bit about sales strategy and riff on some of the important things to keep in mind and think through as you’re developing your own sales strategy.

Vivek: I can see a lot of people joining. Hello, everyone. If you guys can hear us, please give us a shout out in the comments section. If you have any questions for Kent, please do add it in the Q&A tab underneath. Great. Let’s get started then. My name is Vivek, I’ll be hosting the webinar today. I’m a product marketing manager at Hippo Video. Here is today’s agenda. We have a short intro about what Hippo Video is, followed by a quick two minute video.

And I promise I won’t make you take more than three minutes. And after that it’s all about Kent on how to develop a meeting, same strategy. So about Hippo Video, just give me a minute, let me share my screen. 

Okay, to tell you about Hippo Video, the Hippo Video is a video experience platform for businesses, for sales professionals, especially Hippo would help you with video personalization and distribution. Whether you want to shoot a quick door to send your prospects or take an existing asset and send it to all your contacts by personalizing it, Hippo Video would enable you to do that. 

Another important aspect is distribution. You can distribute your videos through emails, LinkedIn, sales navigator on landing pages and also through your actions. So I’ll just play a quick video for you. 


Everyday sales reps send hundreds of mundane text emails hoping to get a response or a meeting. If you are one of them, we know your struggle. However, to prospects, all these text emails look the same. How can inside sales break through this noise to stand out?

Simple! By humanizing your selling with personalized videos. Start by including videos in your sales outreach record. A quick intro video. Edit it online, personalized the thumbnail and send it via email video email humanizes your conversations, makes you look real and gets you those coveted responses to interactive calls to action in your videos to encourage your viewers to book more meetings. Account executives can also make the best use of Hippo video. Include personalized sales pages in your emails to move your prospects quickly through the sales funnel.

Hippo video lets you personalize your entire sales page with the curated content that instantly connects with your prospects. You can send quick video intros, product demos, customer testimonials and contract PDFs on the same page and share it about video. Provides a Real-Time View or analytics to help you see how your potential customers engage based on the analytics. You can easily plan your follow ups and close deals effectively. Video is integrated with popular sales platforms like Salesforce, HubSpot, Outreach, Marketo, Outlook, G-Mail and Mailchimp.

You don’t have to juggle between tabs to set your video sales funnel in action. Using hippo video sales teams can seamlessly convert leads into customers by incorporating videos throughout their buyer’s journey. Isn’t that wow? Use videos to speed up your sales and sell your brand better.

Vivek: That’s all about Hippo Video. Okay let’s dive into the webinar today. Today we have Kent Holland with this. He’s brown and Stanford alumni. After his MBA at Stanford, Kent went on to vote for a top notch company. He started as a business analyst at Deloitte then who handled behind a strategy at LinkedIn, followed by blogs and couldn’t get copper. Kent comes with a wealth of experience in devising strategy, seemed strategy, planning, execution, geekdom, accelerating growth and without a doubt, the best person equipped to talk about today’s topic – How to develop a winning team strategy. Kent it would be great if you could tell us a bit about your role at Copper.

Yeah, absolutely. And thanks for the introduction. Vivek. So I as Vivek shared currently VP of sales at Copper around our global sales organization. We’ve got a sales team currently split across San Francisco, which is sort of our home base today, Toronto, which we’re building out, and then the UK so relatively global. And we also operate in both a direct and partner focused sales motion. So we have both of those considerations to think about. Prior to that, you know, copper actually focuses primarily on the SMB space.

And so the sales motion we have is designed around a high velocity and high efficiency sales motion. And there are a lot of particulars around that. And one of the questions that we’re going to do you into today is how do you think about the differences between an enterprise sales motion versus an SMB sales motion? So that’s my focus today. I prior spent time at Box actually leading our Microsoft partnership. And so I specifically focused on how we went to market with Microsoft and how we sold together to our joint customer base.

Super interesting given Box for those of you who know the company is also competitors with Microsoft, but partners at the same time and so that co-optation environment was very interesting and unique and the focus there was on selling into Fortune 500. So a very enterprise focused sales engagement model, sales cycles that could last upwards of nine months, a year or even longer. And then prior to that, had spent time at LinkedIn helping with sales strategy and new product launches for a team that focused on the 20 percent at any given time of LinkedIn’s talent business that was sort of new product offerings that they were bringing to market and qualifying whether those were going to become part of the core business going forward or things that needed additional support or maybe should be tweaked in certain ways. 

So have experience across different types of sales motions and also thinking sort of high level about how to develop and build a sales strategy that makes sense given the market you’re going after and then taking that to the tactics. How do you put that in play? How do you actually build a team around that and foster team growth that supports that sales strategy? 

Key Factors to develop the winning strategy


Vivek: Brilliant, so to get started with today’s topic, that is how to develop a winning sales strategy. First of all, not all strategies work as planned. And what work for one company may not work for another. Before one decides to go for it, okay I need to develop a strategy. What are some key indicators of the challenge a company might be going to suggest, it is time to develop a new strategy.

Kent: Yeah, it’s a great question! So, you know, there’s certainly some things that I think you could look for that would suggest it’s really time for you to dig into your sales strategy. But I would also posit sort of on the flip side that it’s never a bad time and developing and sort of tweaking and refining your sales strategy is a process you should continuously be going through. I think based on a couple of my more recent experiences, oftentimes the trigger to look into a sales strategy is when you think that you could be doing better than you are.

Maybe you’ve seen a decline in sales, maybe you’ve been stagnant for a few months in terms of your customer base growth. Maybe you’re struggling to attract new customers in the same ways that worked for you three, six months ago. In the case of Copper, we’re primarily in inbound focused sales motion. And so for us, we saw that, you know, marketing leads were growing, but our sales team needed to make sure that we were crisp in the way that we converted them.

And we felt like we had an opportunity to grow the way we were converting those leads. And when we looked at our conversion rates at each part of the funnel, we’ll talk a little bit about KPI is today that are important and different types of businesses. 

It very clearly showed us some opportunities to improve the way that we approached our customers, that we went after the leads that we were getting. And then also the way that we managed our opportunities and so refined our sales strategy and process in light of what we were trying to go after it.

In another case, as we’re thinking about global expansion, there’s a lot of questions about whether you can continue to extend in the market that you’re in or you have to look towards new markets, whether that’s growing into a new customer segment, maybe instead of focusing on SMB moving into mid-market or enterprise or extending geographically and maybe that’s scaling into new regions. You know, for us, we looked at what the viability of our product was across those two vectors and did some market analysis to help us sort of guide the judgment that we want to move geographically.

But all that stems from a need to grow, I think in some cases you’ll be in some sort of acute pain, but in others, we’re all figuring out how to develop businesses that grow. And, you know, I would posit while it seems like, you know, many companies and startups sort of have a hockey stick trajectory that’s always up into the right. That’s seldom the case. There’s always months or quarters where you’re going through some sort of stagnation or maybe you’re struggling to grow in the way you want to.

And I think, you know, if you’re not thinking about developing and refining your sales strategy every three to six months as the market changes, new tools come out, etc., then you’re going to be falling behind. And so, you know, I would suggest that that’s something that you want to say, wait for that that indicator or challenge.

But certainly when you see it, that’s a sign that it’s time.

Vive: Three to six months, you see that as I don’t think a lot of people actually think about it, that they actually as far as you I know. What you are essentially saying don’t wait for any indicators, be more proactive to catch up in the market. 

Kent: Yeah, I think that’s right. I mean, you know, if you and it’s not to say that you’re going to totally scrap your whole sales motion and your wholesale strategy and put that out the window and toss in something new. But there are always little components you should be thinking about refining as an example we’ll talk about lead engagement for inbound. But just using that as an example. 

And really, this pertains to inbound and outbound over the last six to nine months we’ve seen a massive proliferation in SAS applications at a scale that, you know, even in prior years when it was pretty crowded we haven’t seen. 

And now you’ve got all these folks that are trying to get in touch with the same set of leads and a lot of cases and everyone has developed around the strategy of emailing and calling to get in touch with folks. But now you need different ways to engage, you know, Hippo Video is a great example of that, right? Creating a new medium to engage. And so, you know, that’s just one example of a change that’s come around in the last, I would say six to nine months where traditionally, you know, eight to twelve touches on a lead spaced out.

You know, a couple days there’s a playbook around it. But if you’re not differentiating and personalizing it scale now, then you’re not going to be able to drive your conversion rates in the way that you want to. So, you know, that’s a process that we’ve gone through over the last six months and really refined. But there’s always areas you should be looking to to tweak in the way that you engage with your customers. 

Vivek: So before I get into how to design a sales strategy, you have worked with companies that target the enterprise segment predominantly such as Box and now at Copper. I believe you are more focused on the mid-market, SMB and G-Suit customers?

Kent: Yeah, that’s right. We’re primarily focused on the small business segment. To us, I think we align very closely with Google and you know, to give a quick pitch on Copper. We want to help our customers that are on G-suit. We’d be more productive and successful.

We don’t buy by design, allow for the multitude of customizations that some of our up-market competitors offer because we want to drive simplicity. We were built on Google’s material design, so if you can use G suite, you can use copper and we really want to hit it out of the park with contact management, deal management and enabling our our customers to be productive. And so, you know, a typical for a CRM and a two week free trial, you can really get to know what Copper can do.

And so we’re focused on that market. But certainly there’s a lot of differences between the approach we take and more of an enterprise sales motion.

Enterprise vs SMB


Vivek: So very clear a portion.  Anybody who was comfortable using these, then this is the item for you. So having worked in both Enterprise and SMB, would you think I’d see some differences between Enterprise and SMB sales motion? How would they be similar and how are they different?

Kent: Yeah, it’s a great question. So, you know, at the end of the day, in both cases you have products or services that you’re trying to take to market.

And there are a lot of the core foundational sort of skills and motions that are the same. And at a high level, you’re trying to drive business, you’re looking at conversion rates from leads or accounts that you’re targeting through to wins. 

But the style of engagement, the nature of the way you engage with the customer and build out an account is extremely different. Right. So on the one hand, if you’re in a enterprise motion focused on selling into the Fortune 100, Fortune 500 accounts, you know, your alignment is going to probably be one account for a single sales rep.

You’ll spend a lot of time really mapping out that account, getting deep into their needs and really understanding the way that company operates and designing a solution that fits. There’ll be a lot of customization involved and it’s a much more complex sales cycle and deal cycle. Oftentimes the deal values are much greater. So the size of the prizes is there. But it is a very customer engagement. And so it’s a little bit more difficult to drive the kind of repeatability that you look for in the SMB space.

I would say, by contrast, you know, Copper sets really towards the other end of the spectrum focused primarily on SMB. And the impetus is all around efficiency in the way that we approach the market. You know we have a phenomenal product, but it’s also not very expensive and the customers that we’re working with oftentimes aren’t large they’re not, you know, the Fortune five hundreds. And so we need to find ways to scale the way that we engage with our customer base, but also provide the right level of service to help differentiate us in that market.

And CRM, you know, is an interesting solution in that it’s inherently not simple. Right. It’s not complicated as some of our competitors are. But what we’re selling still requires some customization and some level of understanding of the customer’s business and helping them to understand the value that we can bring. So, you know, for us, it’s about how do we design a repeatable motion at scale? How do we partner very closely with marketing to be able to bring that emotion to life and then taking a look at every step of the funnel.

How do we engage with leads and what are the key components of that engagement? At what point do we create opportunities? Having a very clear set of qualification criteria that drive that. And then how do we progress through a very efficient and streamlined sales process? And what are the key milestones of that process through to a win? So I think there are a lot of similarities. You know, at a high level. But when you dig into it, the two motions across SMB and enterprise are very different.

And, you know, having seen it, LinkedIn is a unique example of a company that actually has figured out a way to serve across SMB mid-market and enterprise Box to a certain extent, although Box is a little bit more mid-market and enterprise focused. And that shows and the way they’ve designed their sales motion, it’s primarily an outside sales team. They spend a lot more time really digging into our customers processes. LinkedIn had figured out sort of a hybrid and I think was very successful at doing that.

But I think it’s uncommon for organizations to have a strong muscle across the SMB mid-market and enterprise motions because they do sort of tend to range. 

Vivek: Would it be fair to say for large enterprises, it’s predominantly outbound and whereas for SMBs and in fact it does more inbound, would it be fair to say that or was it by choice of you? 

Kent: Yeah, it’s a great question. So, you know, I think that’s that’s a fair statement, but I think when you dig into the reasons behind it, when you get to the top of the pyramid and you’re looking at the top end of the enterprise market, there’s a finite number of customers in that space. Right. 

When you look at the SMB market, particularly the lower end of the SMB market, there are customers that are creating businesses. Business is coming into space every day.

And so when you have the sheer volume that you have in the SMB space, I think it lends itself to more of an inbound approach where you need to find ways to constantly be engaging in generating interest from the prospects that you want to target in the upper enterprise market. More of an outbound approach is necessary because there’s a lot of noise for those organizations and you also need to get in touch with folks that are relatively senior. They’ve made it obviously up the chain at the organizations that they’re at, which are massive organizations.

And you also are trying to break into accounts. You’re getting very targeted in terms of the folks that you’re going after. There are only a handful of people at an organization that you really need to try and get to. And, you know, there’s a finite number of organizations up at that top space. And so the nature of the way you have to approach them is a little bit different. You can afford to be a little bit less refined in the SMB space, but cast a broader net and drive inbound.

The other thing that I think is important to keep in mind is the average deal size and it’s pretty correlated to the type of business that you’re generating. If you’re selling into an enterprise market, you’ve got a very high HCV that you’re selling and so you can afford to spend a little bit more to drive a custom more outbound approach. Right. You’re spending on an outbound rep that’s only going to be able to generate a certain number of leads or active meetings per month.

And then those will convert, you know, down the funnel. It’s going to take some real time for that opportunity to develop, in all likelihood, somewhere between six and 12 months. But you can afford to take that time in an SMB space where your average deal sizes are lower. There’s a tipping point between where inbound versus outbound actually doesn’t make as much cost sense. So for us, we operate in a space where outbound can be effective if it’s very targeted, but it has to be focused on the customer segments that are going to drive towards the higher end of our deal values.

Because if we align it to our sort of broader ICP, we’re not going to generate enough with just an outbound sort of called email cold call approach. So, you know, what we’re trying to do and what really any company that’s doing outbound today is doing, very few are just doing cold call, cold email with a random list. Everyone’s getting very targeted in the folks they go after in the enterprise space. That means our account based marketing coupled with BTR or SDR outreach, potentially even eight year engagement.

You know, for us that means, yes, very refined lists where we’re understanding exactly which customers we’re going after, which industries, and making sure that’s aligned to our IACP and then going after the target buyers. For the most part, we’re focused on building an inbound machine because the the CCAC, the cost of acquiring customers just doesn’t quite make sense for now in our motion in our space.

Vivek: So you by mentioning about, you mentioned there’s a lot of noise in the market. When a sales team engaging with leads, there is a report that states an average G-suite executive receives over 121 cold pitches a week. And when it comes to inbound the moment a person signs visits a G2Crowd or any other review sites, for example, or even if he signs up for particular product challenges that has to be signed up for can you afford the company does get to know the product.

So when you engage with such lead, how do you ensure that you can stand out from that noise?

Kent: Yeah, it’s a great question. So and I think I’m sure there’s a lot of other sales and go to market leaders on the line that can attest to this. We all have too many tools currently deployed at the organization and we’re getting too many emails from different organizations trying to sell in with a new angle or a new solution that can help us engage with our customer base. So yeah, becomes incumbent upon all of us as sales professionals to figure out how do we stand to stand out from the noise.

And there are different ways that you can differentiate yourself once you’ve gotten that conversation started. But to get in the door, it can be difficult. That’s one of the challenges and why our founding has actually become more and more difficult.

For us, we do it in a couple of ways. I think about the importance, the continued importance of effective marketing and marketing has to be split across sort of the top of the funnel awareness and branding exercises coupled with tactical sort of middle of funnel, bottom of funnel activities, nurture streams and campaigns that are really driving buying signals and surfacing those for sales. But the other way is this concept of personalization at scale and whether you’re doing outbound or inbound lead follow up, it’s critical to find ways to drive efficient, personalized outreach. Right. 

Because all of us only have a limited amount of time in the day. And, you know, coming from experience and I’m sure I’m not the only one I know when you get an email that is clearly a copy paste with nothing customized around your organization or how this solution really fits your specific needs. It’s not one that you’re going to respond to. 

You know where I do respond to the occasional cold or warm email that I get from someone is when they’ve done the research on something that I did or have done in my past through LinkedIn, maybe found an article about something I did, you know, even in my past when I was in college or in business school or the fact that I had to start at one point and you really tie into that and something that, you know, they can sort of connect with me on an emotional level about to drive that initial engagement.

So I think, you know, whereas traditionally and even as recently as, you know, nine months a year ago, there was a lot of, I think, thought leadership around the importance of having a very structured 10, 12 touch sequence that ran over the first couple of weeks or in an outbound scenario, maybe over the course of a month or month and a half where you hit them with a very clear sequence of emails. You know, I can see the thread that comes through.

You’ve either got me with the first couple emails or you don’t. They have to be the right ones. And so I think this concept of personalization at scale is going to become more and more important. And that’s the way that you stand out from the noise. Once you’ve hit a couple of times and not got a response for the most part, and once that person was on vacation or busy, you know, they’ve chosen not to respond to you.

And so, yes, there’s some value from sort of the old tactic of hitting them with ten touches, but it’s got to be personalized. 

Vivek: So when you talk about personalization, the next question that always comes is how do you manage personalization at scale? If I am gonna reach out to say a 5, 10 people a day, I can do an in depth research about the person, get to know the person. But when the volume increases, it becomes hard. How can sales reps manage then?

Kent: And regardless of whether you’re inbound or outbound, I always like to work backwards from what we’re ultimately trying to deliver. Right. And if you’ve been sitting in the sales motion that you have for more than a few months, you should have a perspective on what your conversion rates look like, what your average deal size looks like. And so you should have a sense of how many wins you need in a given period to hit your number or exceed it. How many opportunities and then need to be in the pipeline for you to be able to have the coverage, you need to hit that number.

How many leads or accounts coupled with account based marketing? However, you end up going after opportunities and generating opportunities how many leads you need to have hit to go out to surface the opportunities that you have based on the conversion rates you’ve seen in the past that then defines sort of what you need to do and you can look at your team and say, well, how many leads, how many messages does that mean each team member is going to have to generate per day or per week to be able to to get to our targets.

And it’s a little bit crude. And I think you want to bake in some buffer on what you’re seeing from a conversion rate perspective. But that can then tell you what each person needs to deliver and give you a benchmark to suggest and have the understanding of what realistically a rep can deliver and whether those two are aligned. And if they’re not, it might suggest you need to either build your team or maybe you can actually go after some more.

But I think that’s one way I would think about it. And then I would triangulate that against what you realistically feel the reps capacity is. So you understand what you need to deliver and what you know with the type of personalization you’re going for a rep can do to get it sort of ultimately where you’re going to be. That varies a little bit across outbound and inbound. And I will say that when you’re going with an outbound approach, personalization becomes even more critical and doing additional research becomes even more critical, even though the the response rates are going to be lower when you’re going inbound.

You have the luxury of having a hand-raised or that you’re going after. And so it’s not just personalization at scale, but also time to touch, time to engagement that are really important in an inbound motion. And you can typically get a little bit more efficiency, a little bit more volume out of your inbound responses than your outbound. Great. So the next thing.

Against what you realistically feel the reps capacity is, so you understand what you need to deliver and what you know with the type of personalization you’re going for a rep can do to get it to ultimately where you’re going to be. That varies a little bit across outbound and inbound. And I will say that when you’re going with an outbound approach, personalization becomes even more critical and doing additional research becomes even more critical. Even though the the response rates are going to be lower, when you’re going inbound, you have the luxury of having a hand-raised or that you’re going after.

And so it’s not just personalization at scale, but also time to touch, time to engagement that are really important in an inbound motion. And you can typically get a little bit more efficiency, a little bit more volume out of your inbound responses than your outbound. 

How to access the Target Market?


Vivek: So the next thing is one of the key problems we are not just sales, even marketing, we struggle to learn this. OK. I have crafted a message on my product apportioning statement perhaps, but how do I know that it is resonating with my audience? The target market, I think. Oh, how can I know that? 

Kent: Yeah, it’s. This is a tough one because you never. Assessing product market fit and sort of the fit that you’re sort of ICP messaging has with your target market. It can be very tricky because there can be signals that are misleading all the time. But, you know, and it’s sort of the high level what your guidepost should be always comes back to setting up the right KPI.

So if you’re looking at the right measures from a top of funnel marketing starting point all the way through to the handoff to sales or any of the outbound and work that you’re doing, getting into your sales funnel and then the way that you progress things through the sales funnel, that should give you a fairly clear picture of where you have opportunities for improvement and where you’re actually doing quite well. 

And in cases where you’re struggling to convert sort of broad awareness down into a buying signal on the marketing side or where you’re outbound emails start to really drop in terms of their conversion rate into meetings and converting those meetings then into active opportunities, that can be your best signal for whether or not your message is resonating.

And as you’re tweaking it, you can start to get a sense of whether or not that rate those rates are improving or decreasing. And to a certain extent, you need to find the right balance there because you’re also going to have a lot of other things you need to try and work on throughout the sales funnel. But from a messaging perspective, that’s what I would look at. What are their conversion rates on those messages that are going into market, into meetings and to opportunities.

And, you know, if you’re able to get them the meetings, but ultimately not the opportunities, then that might be a signal that your message is great, but it’s not backed up by what your product can really do because that initial discovery call is not yielding what you want it to. Or maybe you have a sales productivity challenge where you actually need to make sure the reps are geared around the right message. If you’re not getting the initial meetings to start with, that might be a signal that maybe your messaging isn’t there.

But if at the same time you see your win rates are pretty strong and your OP creation rates are pretty strong, then it’s really about how do you bridge that gap to get the meeting. So you have to look at your KPI across the funnel as sort of a picture of how things are going. And a guide as to where you need to engage.

Vivek: It makes perfect sense you break down your messages and see the conversion for each and every message you crack. So in terms of KPI is what Capesize informs your success? 

Kent: Yeah, it’s so we look at a lot and I think, you know, what I’ll say about KPI is metrics in general. You know, obviously there’s been a big focus on deep visibility and data around all parts of the business. And I think that’s really important. I think where it gets a little bit more challenging is within all of the metrics that we could look at surfacing, the ones that are really going to drive your decision making because you can get lost in a world of way too many metrics that actually cloud focus a little bit.

And so what I like to do and I sort of talked about this a little bit is start with conversion rates. And when I look at, you know, what our sales team performance needs to be and whether or not we’re achieving, you know, against that expectation, I’m first and foremost looking at our conversion rates from MQL to win. And I break that down from MQL well to what we call a sales qualified lead, which is effectively the point at which we’ve qualified to lead and converted it into an opportunity.

I then look at a sales accepted opportunity, which is an opportunity that started to progress in the pipeline. And then I look at a win. And so I can see the conversion rates across each of those four milestones. And that helps me understand how my sales team is performing and whether or not the marketing handoff is going effectively. And if there’s different situations, then where certain rates are off, take the MQL to ask you out rate is a little bit lower this month than I can dig in and I want to understand whether it’s a sales productivity challenge or a marketing lead quality challenge and that then I can go deeper from there into source level detail to understand if it’s a specific campaign we ran that’s driving that or is it a specific segment or is it a specific rep? If it’s a situation where are Eskew out to win? Rates are really high, maybe too high, then that tells me we might be choking the funnel earlier on because everything we get to progressing to our sales funnel is closing.

Well, I want to get more into the funnel. Why are we not progressing some of the things that we’re cutting off early on? So that’s how I think about it.

Vivek: Counter intuitive. It’s the first time I am hearing this. Because I never heard if there are too many conversions happening, it might be the time to think about a big product. 

Kent: Yeah. You know, we actually had that situation happen to us in the middle of last year. We saw that our win rates were relatively high. But what we realized was that our conversion rates from lead to opportunity were lower than expected. And I think upon digging in, we spent about three or four months very prescriptively and consciously trying to lessen our qualification criteria. Because what we realized is we were over qualifying before leads really had a chance to progress through the opportunity and us to really get into what the customer needed.

You know, in a 30 minute call, when you’re assessing a customer’s business, especially when we’re talking about CRM, which sits in the middle of their business. But really, this applies to any solution. You have to make sure you understand the full picture before you qualify out. And I think our sales team had been a little bit tight on qualifying so that they were only spending their time on opportunities that mattered. But what was happening is that, you know, we were actually missing out on, I think, an opportunity to.

Yes, maybe spend a little bit more time and maybe have a lesser win rate. And you’re going to take some more calls that don’t end up converting into a win. But at the end of the day, you’re going to close more business. And so, you know, there’s a balance there. But that was something we worked on consciously. It actually helped drive up our MQL to win rate. But what we saw is that our MQL to SQL, all rate went up and our win rate from opportunity to win went down a little bit, but the overall rate improved by about 15 percent.

Vivek: So follow up on that when you see SQL to SAL dropping, what do you think the general problem would be?

Kent: Yeah, it’s an interesting question. So now, I think at every step there are certain things sure you’re going to think about, right? I talked about the MQL opportunity, right. You’re going to look at sales productivity or qualification criteria or is it marketing lead quality if you’re getting a lot of meetings set up and creating that initial opportunity, but they’re not progressing.

Then I think it goes back to something similar to what we were talking about with your messaging. Is your qualification criteria maybe too low? Are you getting too much into the funnel? And then that initial conversation is not yielding anything. Is your messaging off potentially is that initial conversation going in a different direction? And then when they get to know your product, it’s stymied. You know, do you potentially have things that you’re not qualifying for that you should be?

So I think that’s how I start to think about it. And then I dig into some of the tactics with the team and we’ll go through, you know, as we start to identify some things, we’ll test things. But as we identify potential improvements, then we go into, you know, team training and enablement and we have a weekly cadence around what we do there. And so we’re always tweaking different things. Every month I’m looking at how our conversion rates look across this whole funnel?

What does that tell us about the changes we made last month and what we need to do this month? And we’re iterating. 

Building Sales Team

Vivek: Awesome. It was quite comprehensive. Now. Could be better if he can go and do more into culture. How do you build a team? So what about sales team members? How do you build a sales team with culture? 

Kent: Yeah, it’s interesting. I think getting a sales team culture right is tricky, but it’s one of the most important things you can do. And every team culture is going to be really different. So, you know, right now I’m operating in an inside sales motion. And so, you know, folks are in the office. We’re all together on the enterprise side. You may have a distributed team where no one’s in the office ever. Right. You might have folks living in regions that are on the go.

In either case, it’s really important to do a couple of things. I think one is to drive sort of team camaraderie and make sure folks stay connected. That encourages them to stay connected with each other and to the business. But what it does is it builds this sort of unity that keeps people engaged and focused, even when maybe they don’t have as much going on and could sort of lose sight of things that they have that connective tissue. The other thing that I’ve found really successful and this has worked actually in both enterprise or to outside sales roles as well as this inside sales model.

But I’ve found it particularly effective in an inside sales SMB approach is really making sure that the team is involved in decision making. I think there’s a common approach to management in general, and this maybe extends beyond sales.

It’s easy to get into a top down view where you’re sitting in the executive meetings. You have your pulse, your finger on the pulse of the business. You’re making decisions about the way the team’s going to operate and then all of a sudden you go to roll out those decisions. But the team hasn’t been brought along for the journey in the last three months of planning and meetings and all of that. They didn’t really know about that, weren’t involved and it didn’t have a chance to be heard.

So, you know, tactically, I think we went through some of that over the last six months and made a change to really give the team a lot more involved in the thinking behind what we were doing, providing feedback. And, you know, certainly you have to make sure that you walk the line between, you know, letting all of their feedback dictate the strategy versus inform the strategy, which is what it should do.

But I think we found that to be a really effective mechanism for helping people feel a sense of ownership over team operations and team strategy, team direction and everything from the way that we run our weekly cadence now the way that our one on ones are structured to the cross-functional team meetings that we have baked into our calendar to, you know, in some cases the way we even think about our compensation philosophy are now informed in large part by the sessions that we had with the whole team.

And it’s brought everyone into this position where they feel like they have a real sense of ownership over the direction and ultimately the success of the organization in the company. I think that’s been really powerful because it’s difficult. I mean, in a lot of cases, especially if folks are outside sales or younger in their career, you know, they’re still figuring out whether this is an organization they want to be a part of. In some cases, you want to get the most out of them.

Sometimes sales can be, I think, really exciting. But sometimes it can be monotonous and there’s a lot that you have to deal with. And so I think giving people that sense of ownership has been really powerful. But, you know, I think there’s no silver bullet for that. Every culture is different. You have to lean into it. You have to lean into it.

How to make the Target Market work successfully?


Vivek: So this is something I actually saw a couple of days on LinkedIn. This post created quite a bit of buzz and a lot of interaction. So I would love to hear your take on it. So this post goes saying, Okay sales people work hard to meet the targets. This quarter, the they met their targets and next time is bigger. This year and next year, it becomes even higher. And oftentimes they believe that they get demotivated. How do you explain it?

They achieve it but that doesn’t mean it was easy. Yeah. So it is always going to be increasing. And so how do you deal with that?

Kent: Yeah, it’s a great question. I mean, that’s it gets into compensation philosophy a lot because that’s where this seems to come up, where you’ve got a period of strong performance that in effect, then drive management to think about increasing the targets. You know, we philosophically want to have 85 percent average attainment is sort of what we think about. We want to position people that are great to blow it out of the water. And we position our accelerators to enable folks to make a lot of money if they’re great at what they do.

So I think we try and maintain that view and we try and be very tethered in the way that we think about compensation to what’s realistic from the conversion rates that we’ve seen in the past and from the marketing volume given we’re inbound to business, I think in whatever type of business you operate, you have to make sure that you triangulate the way you think about what success means against what’s possible and try and hold back from looking at the performance of a portion of the team or even all of the team as the key indicator of what success should look like. If you know that your team, you know, came into the first quarter and twenty, twenty absolutely crushed it, they were staying late.

You know, they’re working really hard traveling out to take that extra sales meeting when they didn’t have to, you know, putting in time at the end of the month just to go above and beyond. And they came out on top. You have to make sure that you balance that performance against the expectation that you put in place. And so, you know, I try and make it always, you know, aspirational but achievable. And so you have to try and do that.

It’s not easy, but I think, yeah, you walk a fine line because if you get into a position where you’re continually raising quotas, that can be very damaging to a team, certainly very demotivating, as you said. So I think you want to try and set the expectation that you’ve done your research on what’s realistic. You’ve put that in place and the team can go get it. I think the other thing that is helpful is to try and maintain some level of consistency, both in the way that you structure compensation, but also the targets themselves.

You can’t keep changing the goalposts. If you keep moving the goalposts, then you’re going to find that the team never really feels like they have a good handle on what they’re supposed to do. Never feels like they can be successful because every time they are successful, you’re changing the definition. So you have to try and maintain some continuity there.

Vivek: So you’re talking about doing a lot of experiments and staying nimble. How do you remain nimble and continue to play on these until you find what works? While at the same time keeping the people excited about what are you doing, and also keeping them motivated? Because the team should have a sense of what works and what doesn’t. But again, I go on to a different strategy. So how do you keep your nimble?

Kent: Yeah, it’s a great question. I think it goes back to the answer that I was talking about for your previous question on building a culture of success. I think it comes back to making sure the team feels a sense of ownership and is involved in the thinking. And not only is that important in terms of keeping the team engaged, but it’s actually important for you arriving at the right outcomes because, you know, for those of us on the phone that are leading the teams, we’re not on sales calls every day in the same way that our team is.

They’re the ones that are on the front lines talking to prospects for the first time. You know, we fly in for, you know, maybe the bigger accounts and the demos that are happening with those companies or maybe for pricing conversations. But at that point, a lot of the learning has already passed. And so I think it’s really important that you start with an understanding from the team about some of the things they think we can be doing differently.

You know, how can we make changes that are going to impact their day to day, make them more successful, better engage with the prospects that we’re talking to. What are the biggest pain points that are coming up? Where do customers get a little bit confused or lost on a call?

And what can we tweak? And so I think if you surface that from the team, you’re actually going to find that there’s a lot of great ideas and those are really, really important to have. That’s also the beginning of making sure they’re involved. And part of the process of iterating and testing. And from there, I think you have to be very focused on just a couple of things that you’re going to go try and tweak both because change is very difficult for folks.

And so you have to be very tight on change management. But also because if you’re going to learn from some of the changes you’re making, if you make more than a couple changes, it’s very difficult to know what’s working and what’s not. So you have to be cognizant of that. And then throughout the process, I think it’s maintaining that tight transparency with your sales team so that they know that they’re the ones that are really helping to lead these changes.

And, you know, whether it’s a success or a failure, we’re gonna be in it together. And the sales team should be celebrated in the successes that will ultimately come from those changes.

Vivek: I think that’s one of the questions we have, I think we can dive into the audience’s questions right now.

Kent: Yeah, I’m happy to take any that are on the chat. 

Vivek: So the first one is the GDP kicking in. What are the ways you are getting leads into the fire?

Kent: Yeah, that’s a good one. So what GDP R, California, we have a Data Privacy Act coming into play as well. It’s a really, I think, important time for us to make sure as a sales organization and group of sales leaders that we’re tight on the way that we manage personal information for us because we’re in in-bounds focused business we have clear terms of service where GDP is compliant in the way that we message and market to our customers. We’re encouraging them to start a free trial or requested demonstration. And then when they do, we’re following up via email or phone that they’ve provided.

So we’re not pulling any information that they haven’t shared and given us consent to leverage. That’s not always the case with some of the other tools that are out there that will provide email and phone lists to go after and and targeted accounts. But I think you have to be very careful. It depends on the space in which you’re operating. But certainly if you’re going after and building a sales strategy, a sales motion that’s global, you have to be very cognizant of the global policies that are in place and make sure you’re adhering to them.

Those are going to continue changing. I think ultimately they’re going to have an impact on the way we approach the market. So I think the best I can offer is that you’ve got to be very cognizant of them and make sure that they’re accounted for in your design. The next one is what is a playbook you would recommend. Believe it is the strategy. 

What is the Playbook Strategy?

Vivek: What is the playbook? The playbook you would recommend you know? 

Kent: I don’t have a one size fits all playbook. I think that, you know, the style that I aspire to is grounded in data first. So I look at assessing the sales motion that you’re building or that we have internally or that, you know, any anything I would look at, I would start with an understanding of what the key milestones are in that process from the top of the funnel through to current customer and beyond, including sort of onboarding activation and ultimate expansion of that customer. And I want to understand from both a revenue and a logo perspective how our prospects and customers progressing through that funnel, that’s going to then give me an understanding of where there’s opportunity to improve based on what’s in place.

I think whether it’s an SMB or an enterprise organization and the deal size and typical deal cycle is going to give you insight into what type of structure you need. There’s a certain threshold, I think, around 10K based on some of the research that I’ve done and thinking about it as to where an inbound motion versus outbound motion makes sense. And so if your HCV is around 10K or above, I think it makes sense to start thinking about an outbound motion where you can have BTR that go after a target account list.

They create ten to twelve opportunities or meetings per month. Maybe that converts to, you know, four to six opportunities, etc. So you can map those out. I think you just have to triangulate though from a bunch of different directions. There’s not a one size fits all sales playbook, but there are important things that you need to do along each milestone or each part of the process. And I think start with data, lay out what those key milestones are for.

You understand where your HCV is and whether that’s, you know, more along the lines of SMB or enterprise that will inform the team structure and whether you’re going to have SDRs and areas or are you just going to have inside sales reps? Do you need solutions engineers? How technical is the sale? So that will give you a good context on sort of the core structure. And then from there you’ve got to just develop and iterate a little bit.

You’ve got to understand where you’re successful and where you’re not and where you’re not. Then you can dig into how to provide more structure, give your reps more support, more training partners, better with marketing partners, more closely with customer success. You’ll have to read the the the writing on that one in terms of the metrics as they come out in line with what you’ve put in place.

Vivek: The next question is about Copper CRM. So how is that differentiate Copper from Salesforce?

Yeah. Great question. So I get to talk about this one every day. Interestingly, the conference Salesforce plans two very different spaces. So if we’re in the same conversation, there’s a little bit of crossover, but more than likely one of us is in the wrong conversation. At that point. We’re purely focused on G suite and what we’re focused on doing is operating at the intersection of CRM and productivity. So imagine two sorts of circles that form a Venn diagram, CRM on one hand, productivity on the other. We want to play where those two meet.

And so, you know, we do contact management really, really well with our G suite integrations. All of your email and contacts can be automatically syncs with no data entry required. We do pipeline and deal management really well. So we have a Kanban style view. It’s very user friendly and you can track all of your sales opportunities. But we also enable you to attach your G suite documents to wreck a person record or an opportunity record. We have great task management and so we provide this sort of productivity layer underneath.

And from a product development perspective, that’s a big area we’re investing because we want to help our customers, our SMB customers be more productive in the way that they work with their customers. And we believe that they should be organizing or that we should be organizing all of our work around the relationships that we have and enabling the people to do the jobs that people can do best. And so not spending time doing data entry, complex mapping, having a salesforce admin that has to sit in there.

We want to give you a tool that works, that focuses on allowing you to do the jobs that you’re focused on doing. Not just one that helps you map out all of your sales and then your success team and your customer service team. So that’s sort of our focus and again, squarely in the SMB space. 

Vivek: Actually, this is something I’ve personally seen whenever there’s a meeting between marketing and sales, the number one question is CRM, it’s not updated. The answer is we don’t have enough time. How can it be addressed?

Kent: Yeah, totally. I mean, we’ve done everything we can with G Suite to automate the way that all of your emails, your calendar invites, your hang out meetings get sent back into the tool. And so it’s very easy to have visibility on any contact or opportunity record without having to add anything.

And we integrate with VoIP providers. So all of that sort of automated data entry is a key part of this. Right. And enabling people to get time back in their day so that they can focus on engaging with customers, engaging with partners in the ways that they need to do. 

Vivek: We have more questions. So, when you are targeting large enterprises, what are the inputs or areas sales should collaborate with marketing?

Kent: Yeah. It’s a great question. I think, you know, the is in the marketing approach and this is a broad generalization. But in a more inbound SMB world, the marketing team needs to be sort of focused on two things. One is branding and awareness. The other, though, is very tactical. Lead generation. And so the way that they structure campaigns and drive leads is very important. I think for an enterprise and an enterprise motion, there’s an equal tie in with marketing.

Certainly brand and awareness become really, really important because you need to be able to to be seen as a key player in the enterprise space, be seen as a brand that’s going to be around for a long time that that they can rely on that’s trustworthy. So you’re building that brand, but you’re also a partner in actually a lot more closely on more targeted campaigns, account based marketing outreach. And so you’ll have sort of the always on campaigns in the same way in SMB organization might.

But you’re also going to be partnering more closely with specific sales teams to do account based marketing into Fortune 500, making sure you have a list of the 10 target profiles within each account you’re going to go after. And potentially marketing can play the role of sending that first personalized outreach out if the BTR team can’t. And so they start to partner very closely with your sales development and business development teams. But I think they should be looked at as a real partner in that.

I think a lot of times there can be a lot of finger-pointing that happens in any type of organization, but in an enterprise organization where there’s not often as seamless of a tie between a marketing campaign that generated a lead that sales closed within a month, that just doesn’t happen in the enterprise space. Marketing is a critical component in the success of a sales team. Marketing plays a big role. Thinking about many channels through which you can engage with prospects is a critical component in enterprise and marketing fulfills that. 

Vivek: That sums up the questions we have. Thanks a lot Kent, for joining us today. I personally had a lot of questions and got answers, especially on messaging. Guys if you are using G-Suite CRM, check out Copper, they have a 2-week free trial. Kent and where can we follow you?

Kent: LinkedIn is probably best. Thanks for hosting me Vivek, thanks for the opportunity. 

Vivek: It was a great session, Kent. Thanks for joining us.

Kent: Alright. See you soon.

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