Dennis Dresser – High Performing SaaS Sales Orgs – Ep.214

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(00:00:00) – Intro

(00:03:17) – Career lessons learned

(00:06:27) – Evolving a Sales Team

(00:08:14) – Churn impacts

(00:10:10) – The high-performance sales framework

(00:14:28) – Characteristics of successful Salespeople

(00:15:58) – Hiring in Sales

(00:18:29) – Is there one skill or quality you’ve been able to coach up?

(00:21:17) – The Sales Qualification Methodology

(00:23:50) – What are some effective ways to involve those outside of Sales in the process?

(00:25:43) – Where do you see Sales Teams most often get stuck?

(00:29:15) – Characteristics of a high-performing prospecting function?

(00:32:14) – The future of content marketing

(00:35:04) – Advice to CEOs and heads of Sales teams

Alex Bridgeman: You’ve been a part of a lot of different sales teams, both as an executive but also as a investor and advisor. I’d love to hear kind of maybe some of the things you’ve learned in the different career opportunities that you’ve had so far.

Dennis Dresser: Absolutely, Alex, thanks for having me on the show. I’ve been very fortunate to work for some very high performing companies, both public and private, and been surrounded by incredible mentors, executives, and peers as well. And so, over the course of the last 25 plus years, I’ve taken a lot of the learnings from the experiences and built what I call a high-performance revenue growth playbook, which I’ve then deployed to multiple companies where I was the CRO, as well now with our portfolio companies. I’m an investor and an advisor in private equity SaaS companies, very early stage as well as growth stage. And so, it’s been really rewarding for me to wear a different hat now as an advisor, working with the executive teams, working with the heads of sales in these portfolio companies, and again, sharing all the lessons learned and best practices with them and helping them really drive profitable growth.

Alex Bridgeman: What were some roles where you feel like you had the greatest learning curve?

Dennis Dresser: I would say when I started at Eloqua, a marketing automation company in 2010, it was my first SaaS company that I had joined. And so, one of the things that I learned very quickly was we have to earn every dollar every day because it’s a subscription-based company. And so, it wasn’t just on-prem where you could sell the software and then move on to the next prospect and not necessarily worry about adoption and an ongoing customer satisfaction and success. You obviously had to continue to engage them on their customer journey, through deployment, through adoption, and ultimately through ROI, which I thought was a great learning for me in terms of building this value-selling methodology and really helping our prospects identify those key metrics that they need to address with our software, and ensuring that we have, again, an implementation plan and a success plan to continually tie back to those metrics to make sure jointly as partners, we’re moving the needle, whether it was on acquiring new customers for them, or if it was generating net dollar retention, whatever those metrics were, we would make sure that every touch point we had through their journeys, again, as a customer, that we were implementing the right processes, they were leveraging the right features and functions to ensure that they were getting that expected ROI. So that was, again, probably the biggest learning is working with the customer success team post-sales on that continual journey.

Alex Bridgeman: What kind of changes did you make to the sales team knowing that the sales process doesn’t stop once they become a customer? There’s this ongoing making sure that they’re getting ROI from the product and they’re using it properly and customer success is clued in. What changes had to happen to your sales team to make that an effective overall process?

Dennis Dresser: We had to document in pre-sales more than we probably ever did in the on-premise world, meaning using our CRM, we would document those key metrics. We would document desired outcomes that the prospect would have with our software. We would make sure that we had really good handoffs between our sales team and our solution consultants to our delivery team, and in fact, bring the delivery team into pre-sales at a certain stage. Normally, it would be sort of the scoping stage of the sales cycle. But again, that transition, that handoff in terms of documentation, in terms of conversations and then really kickoff calls. Once we actually landed the new prospect, we had a kickoff call. We would really demand, if you will, that we bring both executives that sponsored the project on to the kickoff call, so we had that alignment around the delivery plan, around what was the most important outcomes that they were looking to address. So, I think that handoff between sales and our delivery team and success team was something that we really drove accountability on the sales rep to really own.

Alex Bridgeman: Yeah, it sounds like bringing on the executive sponsors into those onboarding calls would, I would think, help reduce churn. Were there other activities along the process that you noticed or could measure an impact on churn?

Dennis Dresser: I think the ongoing, so whether it’s a monthly or quarterly customer success review, I saw a lot of companies would not bring in the executives to those calls, just the users, but I think it’s really critical. We found that companies, my companies as well as [Porco’s? 6:02] that actually have follow-up touches with both mutual exec sponsors, again, prospect executive that was really going to be funding the project that was responsible for whatever key metric we were solving for, as well as on our side, having a key executive involved to shadow and shepherd those customer success reviews, again, throughout that journey, was I think a really critical factor in getting the desired return investment, getting really high gross retention with that customer. So, I continually espouse that as a key best practice, especially, of course, on the larger accounts, larger customers, larger ARR opportunities.

Alex Bridgeman: Is there an ideal cadence, whether between monthly, quarterly, or biannual, annual, that you’ve found to be the kind of right sweet spot for frequency? Or is it product dependent too?

Dennis Dresser: It’s probably product dependent, as well as like the customer size and complexity dependent, but I found I think quarterly is the right cadence at the executive level. Certainly, it’s a more frequent cadence at the user level with the customer success team. But certainly quarterly, I think, building a more structured, formal customer success review, executive level presentation on a quarterly basis to check in and making sure, again, we’re mutually tracking. I think that was the right cadence, right sweet spot.

Alex Bridgeman: Can you talk a little bit about the high performance sales framework you’ve put together and what are the key elements of it?

Dennis Dresser: Certainly. So I have a framework that I use, which is called People, Process, and Performance Management. And so, when I think about developing a high-performance team, I think first off on the people, what are the right ideal candidate profiles that we need in the sales organization based on doing some profiling of our high performers in the company and then obviously wanting to replicate and build the team and scale the team with those types of profiles. And then processes, looking at our sales process, understanding where we’re executing well in our sales process, be it discovery, be it demoing, be it in solutioning, and where we’re not doing well. And we can then determine where we’re doing well and not doing well based on looking at our conversion and velocity from stage to stage. And so, we instrument our CRM to be able to report, as well as using BI tools, to be able to report on that conversion and velocity. And we start with creating a baseline. How are we converting and how fast are we moving deals down the funnel today, and then benchmarking ourselves. So, I’ve been lucky to work with a variety of SaaS companies and also having a lot of research and data that I could then apply to my specific company based on what stage we are in our life cycle, what’s the complexity of the products that we sell. So, use those benchmarks to then set goals for our team and our individuals on executing down that funnel. Then performance management, let’s establish those dashboards that show us the leading indicators on those key metrics and stop letting how we’re doing and then put a cadence in place around pipeline forecast management. And we do it at an organization level, we’ll do it at an individual level so we can start stack racking individuals and really identifying where individuals are really falling short across those key conversion and velocity metrics. And that shines a light on what skill gaps we have. Do we need to do some discovery training? Do we need to do some training around better negotiations? So, it’s a pretty well oiled playbook and performance management structure that I’ve been able to really fine tune over time to, again, build, scale, and execute in a high performance sales operation.

Alex Bridgeman: What’s the most recent adjustment that you’ve made to your playbook, most recent refinement or learning that you’ve included with it?

Dennis Dresser: What we found, especially in this last two years where it’s a more challenging market for sure to sell into, that value selling, which really is focusing on engaging these prospects, early top of funnel, and being able to really spend more time doing discovery on those key metrics that they need to address in order to hit financial goals, for example. And so, I think what we’ve had to do with the team is develop some curriculum, some training to help them with some business acumen to effectively engage with business owners, business executives around those metrics in their business. Historically, I would say, most teams are built with more feature function selling skills, and that was probably fine in the previous eight years where it was sort of the growth at all costs and there was a ton of demand, but certainly, the pendulum has shifted significantly the last two years. Companies are actually rationalizing the amount of technology they have. And so, we really needed to focus more on value selling skills. So that’s been a real big shift the last two years, I would say.

Alex Bridgeman: And taking a look at that first P, the people, what are some characteristics you found are common across successful salespeople?

Dennis Dresser: Definitely. Hungry, humble, and intelligence. Those are sort of, to me, foundational profile attributes that correlate to our high performers. Beyond that, we look at have they had a consistent track record of hitting goals? Have they had experience as an athlete, as a musician, those are really- and where they had to fine tune whatever craft that was, what was their training regimen, and tell me, walk me through that training regimen and what were your goals and whatever that ambition was. So, we’re looking for people that are very ambitious, that have a really good work ethic, even previous to coming into corporate America. So those are some of the attributes that we found that correlate well to high performers that we’re looking for when we’re sourcing and building our people organization.

Alex Bridgeman: So, we’re going through a hiring process now for a salesperson at HW. And one thing I’m struck by is that there’s not necessarily one person who checks every single box that you’re looking for. You’re more kind of weighing certain skills versus another set of skills that might not have much overlap or some overlap. How do you weigh different candidates who they might have those qualities but then stepping into experience that maybe they know your industry really well but they’ve never sold or they’ve been a really successful seller but don’t know the industry? How do you kind of weigh the different experience, sales experience, industry, technical expertise? How do you weigh some of those qualities?

Dennis Dresser: Yeah, that’s a great question. It’s really, my experience at Anaplan where we were growing the company at sort of 3x every year, which required me, of course, to grow sales capacity at a clip that is very challenging when you are just trying to source one type of profile. So, what we had to do is actually identify and design what ended up to be three different ideal candidate profiles. And to your point, one profile was folks that came from the domain, in this case it was finance. They might have been consultants. They had no sales background. And so, we designed these three different profiles. One is your typical sales athlete that came from a long history of selling in the enterprise. The other one was folks that had experience working in finance or doing finance consulting. And so, what we did was we designed a sales academy to help those folks that didn’t have a sales background quickly develop those foundational sales skills. And we did that internally with our onboarding and enablement folks, but we’d also look at third parties. There’s plenty of sales training firms that you can bring in to help. But that was really critical to our success, making sure we had that sales academy for folks that didn’t have those foundational selling skills. And then I would say on the flip side, for those that don’t know the domain, we also have them spend time actually post sales in the customer journey to learn the customer use cases, how they deployed our software to start to learn their lingo, be at the office of the CFO. I think having customer engagement as part of the onboarding process was really critical for those folks. So bottom line is you can tailor onboarding and enablement based on those different profiles. And you need to, to really successfully get everyone up to the same level, which is amazing selling skills and also being very credible in speaking the customer’s language.

Alex Bridgeman: Have you found that there’s one skill or quality that you’ve been able to coach and teach up pretty effectively that maybe on the surface seems more difficult? For example, we might have someone who has been a really successful seller, but they haven’t sold in real estate before. They’re not familiar with the space. We think we could train that person up, and then, vice versa, lots of real estate, no data experience. How do you measure or value the difficulty of different qualities to train?

Dennis Dresser: Well, as you know, vertical SaaS is in vogue. And there’s plenty of industries that are ripe for disruption for SaaS. And so, we’re seeing sales folks having to pick up, to your point, a new language, a new industry language, be it real estate, be it construction, be it healthcare. And it is a challenge because that vertical speak, I think, is something that doesn’t necessarily come natural to all of us. And that’s back to my point on having them engage in and learn customer stories, having them speak to customers, which is like shadowing, customer success calls, providing them any type of enablement research, have them go to conferences. It is critical because what I’ve seen to be another common attribute of high performers is, especially kind of in the enterprise, this more complex buying process, you have to be very consultative, really critical to become a trusted advisor. And that means you have to understand their industry. You have to understand their business processes. And so, the other way I’ve done that is working with third-party consultants, which we typically do try and build an ecosystem of third-party consultants that are either advising prospects on a different approach using our software or helping us implement, and so scaling out the professional services team with third parties, they typically have that domain expertise. And so having sales reps do four-legged sales calls where they let the consultant kind of drive the conversation, and hopefully by osmosis over time, they’re going to pick up on that language. So, there’s various ways, I guess, to help sales reps pick up that vertical speak that, as you know, we’ve just talked about, I think is really, really critical for them to be credible in the sales process.

Alex Bridgeman: What’s the four-legged sales call? What’s that mean?

Dennis Dresser: Oh, just meaning the sales rep has two legs and the consultant has two legs.

Alex Bridgeman: Nice, nice. I like that. You also talked about a sales qualification methodology, MEDDIC, right?

Dennis Dresser: That’s right. Yes. So I was exposed to MEDDIC I think probably at IBM actually. When I was at IBM in the early 2000s, we were very acquisitive. We had bought a lot of software companies. It was a challenging time in the market to grow not organically, so sure enough, the big companies were highly acquisitive and grew through acquisition. And so, what we did is we bought companies that had incredible sales methodologies and processes. And one common one that we found was MEDDIC. And that came out of executives out of PTC that ultimately left and started and were key executives at a lot of different software companies to this day, still are. And so, we found that this was a methodology that, once we had a validated opportunity, it was a great framework to train reps on how to execute in the sales cycle, uncover some gaps and some blind spots that we had to effectively close the opportunity. And so that was, again, a methodology that we would train, that we would instantiate in our CRM system and then use in key deal reviews, which is another aspect of a high-performance culture, is having some cadence where you bring in anyone involved at the company in sales. And frankly, everyone, I think, should feel like they’re in sales. So that could be executives, could be the CMO, could be product executive as well, that we would establish usually a monthly or quarterly key deal review. And we would have the reps go through the MEDDIC qualification of the opportunities and then coach and inspect and drive to key actions around where we had gaps, whether it was the decision process, whether it was the metrics, whether it was we didn’t have a really strong champion. But again, it’s a great methodology and framework to use to help companies improve on opportunity conversion and forecast accuracy.

Alex Bridgeman: So, you kind of touched on an interesting point there, which is how do you bring other folks from the rest of the team, rest of the company into sales so they can kind of get a peek into what that process looks like and what prospects are saying and whatnot. What are some effective ways to do that, to involve other folks from the rest of the organization on somewhat of a regular cadence?

Dennis Dresser: Yeah, there’s two ways that I’ve done that historically. One is through an executive sponsor program. So, when we kick off a quarter, we identify the top X amount of deals that are what we call must win deals. And then based on the profile of the company or of the buying executive, we would like to, we would map our executives across function. So, it could be marketing, could be product, could be finance, whoever. But ideally, you assign a couple of key deals to each of our C-suite. And then from there, we would have, as I said, a monthly cadence where we would then do a deal review and those executives would get exposure to our win plans. And then they would have a role engaging the prospect at certain points of our sales process. And they would feel accountable, just like the sales rep felt accountable. So, we drove accountability across the whole C-suite on specific deals. And then the other, of course, benefit is that they get exposure into the market dynamics, whether it be competitive dynamics, whether it be pricing dynamics, whether it be kind of product gap dynamics that we have, that then helps them formulate their key initiatives in their functions, where they need to prioritize to help us obviously win in the marketplace. So, it really is a great process to institute is this executive sponsor program and then key deal review cadence that would be an important outcome from that.

Alex Bridgeman: Yeah, I like that a lot. I hadn’t heard of a version or a framework like that, but I like that idea. Where do you see sales teams most often get stuck as they try to grow their headcount?

Dennis Dresser: Finding those profiles that we talked about, whether it be two, three, four of those ideal candidate profiles. It is just trying to figure out where do you source. And what I’ve suggested is the best way to actually source is use those sales reps that you have that fit that profile and have them help you. They likely have peers, friends, acquaintances in their network that fit that profile. So, one thing that we did when we were in hyperscale mode is we would actually have these sourcing blitz days where we would have the sales reps come in to the room and actually go through their LinkedIn, create that target list, and then do some outreach with us to try and generate candidates into our funnel for building the organization. So, we looked at people just like opportunities, and we had a cadence, we had target lists, and that I’ve found was a really great best practice when you’re in kind of hyperscale mode of building the organization, and leveraging your people, your sales reps, to help you build that funnel of candidates.

Alex Bridgeman: I like that a lot. What about when as the company itself grows or attempts to grow and cross certain revenue hurdles, what often gets in the way or what often becomes more challenging?

Dennis Dresser: A couple of things. One is executing a multi-product go-to-market strategy. It’s critical. Typically companies, they start with one product, they go to market, they get success, and then where do they go from there? Well, ideally, you’re building more SKUs or you’re acquiring other companies. But ultimately, you want to move towards more of a platform go-to-market strategy where you have multiple SKUs and you’re able to get more wallet share with your existing customers. I find that a lot of companies don’t have that playbook, call it the land and expand playbook. And so, I’ve been able to develop that, again, through these great company experiences, through working with a lot of great executives. So, I try to help companies with that land and expand strategy because, again, normally you don’t see that companies have that inherent necessarily in their organization in terms of that skill set. The other thing is marketing source leads, sort of inbound leads, eventually we see that that well runs a bit dry of people in the market actively raising their hand that have real funded projects. And so, you have to then develop an outbound playbook for your sales organization. Again, I find that to be a challenge, an obstacle that most of my portfolio companies find. And so, I help them with that exercise as well. But it’s a heavy lift. Both of those are not easy to do. It does take kind of cross-functional collaboration. And it’s really critical though.

Alex Bridgeman: Yeah, I remember being on a call with a company that you’re on the board of, and they had a whole team of BDRs who were doing like 50 calls a day or something. They clearly had some sort of like a pretty strong outbound process going. What are some of the characteristics of a really high-performing prospecting sales function?

Dennis Dresser: Yeah, I think, it’s multi-medium. Folks a couple of years ago got really caught up in just batch and blast. It was all email based prospecting. And so now, as you know, we’re all inundated with so many outreaches through our email. And so, what I’ve understood is the conversion has really dropped significantly around email prospecting. And so, we’ve now looked at building back that old school calling culture as well as using LinkedIn and in-mail, using videos. So just try, A-B testing different forms of outreach. And then as folks are constructing their multi-touch cadences and outreaches, in the tools, the new tools that we have, it’s got to be a combination of calls, in-mails, emails. It’s just one size doesn’t fit all is the bottom line. And so just finding what works the best, sharing those best practices across the team, whether it’s in-mails or videos, or whether it is just calling outbound. Another challenge to that, of course, is that most companies are now remote. So finding their mobile numbers is certainly not easy. And so, I think there’s now tools that you can acquire that have mobile numbers as well. And that’s important in terms of that data enrichment. But yeah, it’s not easy, but there are some really good playbooks out there, I think, around the outbound motion that people can rely on and leverage.

Alex Bridgeman: Yeah, I’ve recently been testing Loom videos, and the interesting thing about Loom videos is when you send it, you know when they’ve watched it because Loom will tell you, like, hey, you got a view on your video, and you can make it really customized. What are some of the most creative prospecting experiments you’ve seen folks do?

Dennis Dresser: Yeah, I’ve seen videos work, as you said just now, mostly with in-mail that I’ve seen. I think, again, it’s just more engaging. And so I think we’re seeing prospects respond to those. I think you’re trying to engage them in a different way than your competitors are. I think also the other thing that I’ve seen work well is that companies want to learn from the best companies in their industry. And so doing webinars is another great way to generate demand where you have your feature, your best customers, and hopefully they have brand names, and they talk about their journey and their successes. And so, I think that’s been a great way to get prospects also into your funnel is through these customer webinars that the companies are doing.

Alex Bridgeman: Do you see content marketing continue to work, kind of like along the lines of webinars or newsletters, company podcasts?

Dennis Dresser: Yeah, absolutely. People are hungry to get educated, to figure out how they can be best in their craft, in their role and generate value for the company. And also, as I said, learning about what are the key dynamics and what’s happening in the industry that helps them be more progressive. And so, I’ve found that commissioning white papers with like the McKinseys and the Bains of the world were really helpful, high value pieces of content that I could repurpose through various marketing campaigns. So I think that’s a good best practice that I found prospects really appreciated from a content perspective. And so, I think companies are doing eBooks relative to a variety of topics, again, mostly focusing on the buyer persona and helping them become more proficient in their role. I think that resonates really well.

Alex Bridgeman: You said commission, like a white paper with a consulting firm like McKinsey. How does that work? What does that end product look like?

Dennis Dresser: There’s these total economic indexes, or I forget what they call them, but there’s like different forms of these white papers, that, as I said, talk about a little bit of a business case for doing something different than you are today, what the potential ROI can be. And so those are like some of the content in these white papers. And typically, it’s you reach out to McKinsey, one of their various vertical practices, or it could be horizontal practices, depending on, of course, what you’re selling. You find one of those consultants and then usually pay them a fee. They’ll figure out how to scope this with you, and then you pay them a fee, and they’ll collaborate with you on some sort of engagement to create the content. And the fees range, obviously, but again, it’s been tried and true way to create, I think, a very, very high-quality piece of content is working with these consultants, these management consultants.

Alex Bridgeman: That’s interesting. I wrote down that idea because it kind of spurned the idea of some other-

Dennis Dresser: Total economic impact, that’s what it is. It’s TEI, yeah. And so, you’ll see out in the marketplace, if you go to probably various technology company websites, you’ll probably see these TEI studies on their website that they make available. And then of course, they’ll use them probably in some email campaigns as well. But that’s one variation of this high value white paper that I talked about.

Alex Bridgeman: Yeah, that’s brilliant. As a closing thought, what couple pieces of advice do you find yourself commonly or most often giving to CEOs and the heads of sales teams?

Dennis Dresser: People, most important thing is getting the right people on the bus in the right seats. So you should have some cadence where you’re analyzing how you’re doing against that, where are your gaps. And I think bringing people in, especially as you start at early stage and moving into growth stage, you definitely need to have key executives that have what I call seen the movie before, hopefully a very successful movie. They can bring in learnings and best practices as opposed to what I’ve seen is a common, I won’t say failure, but I think issue is that companies promote from within to those key executive seats. And they’ve grown up only at one company, have only seen one movie. It’s important to have executives who have seen a variety of movies, ideally successful. So having the right people, building the right people in the right seats is really the most important thing from my experience.

Alex Bridgeman: I love that. Dennis, thank you for coming on the podcast. I really appreciate it. It’s good to chat with you and meet you. And I look forward to chatting again more soon.

Dennis Dresser: Thanks Alex.