PODCAST 148: What Makes a Great Sales Leader with Hunter Madeley

If you missed episode 148, check it out here: Lessons Field Sales Can Learn From Inside Sales with Kristin Twining

Subscribe to the Sales Hacker Podcast

Show Agenda and Timestamps

  1. Show Introduction [00:09]
  2. About Hunter Madeley and Vena Solutions [1:42]
  3. A good path to the CEO’s spot [9:23]
  4. Surprises in the top job [17:32]
  5. Hunter on lessons learned during COVID [19:19]
  6. The keys to successful agile planning [23:16]
  7. Sam’s Corner [34:47]

Show Introduction [00:09]

Sam Jacobs: Hey, everybody. It’s Sam Jacobs. Welcome to the Sales Hacker Podcast. This week, we’ve got a great show for you with Hunter Madeley, the CEO of Vena Solutions. Hunter is a long-time sales executive and sales leader at HubSpot, helping take them from $80 to $600 million. He was at Salesforce when it went from $2 to $4 billion, and he helped grow the Canadian business of ADP from $30 to 300 million. Hunter has had a hand in massive, enterprise-changing growth over the course of his career.

Before we get there, we want to thank our sponsors. Our sponsor this week is Outreach, which has been a longtime sponsor of this podcast. They just launched a new way to learn Outreach on Outreach. Now, you can learn how the team follows up with every lead in record time after virtual events and turns them into revenue. You can also see how Outreach runs account-based plays, manages reps, and so much more using their own sales engagement platform.

Now for some other great sales ideas in my conversation with Hunter Madeley.

About Hunter Madeley and Vena Solutions [1:42]

Sam Jacobs: We like to start off with your baseball card. Really it’s an opportunity for you to tell us a little bit about what Vena does in your words as the CEO.

Hunter Madeley: One of the most important things a leadership team can do is make sure that their strategic, operational, and financial plans are married well together. At Vena, we think of ourselves as a point of view on how to do that really well, and then the technology to back that up. Think about finance teams and the way they work together to kind of build out all of the budgeting, forecasting, and planning and how they hook that into the actuals, sales data, and other data.

Effectively, we’re a set of tools that allow companies to plan the way they want to grow. Our job is to partner with our customers to give them a point of view on how to best plan and grow their business. Then give them the toolset to allow them to manage that process and leverage data and analytics to make good decisions.

Sam Jacobs: How old is the company?

Hunter Madeley: We’re about nine years old. We were started by three local Toronto founders that had been in this space for a number of years and had a point of view on how to build a great product and hopefully a great company.

I’m just honored to be taking the baton from the former founder CEO. Over the last 18 months, I’ve just been privileged to be a part of a pretty special culture and a great Toronto-founded success story. I think we’ve got lots of years of scaling and growth ahead of us.

Sam Jacobs: That is exciting, and the website for everybody out there is venasolutions.com. It does look like the suite of solutions is pretty robust. Tell me if I’m misunderstanding, but that implies that this is really an enterprise grade solution for large companies that have a lot of different disparate processes. Is that accurate?

Hunter Madeley: It’s actually an interesting discussion because the platform itself is wired to support customers of any size. Early on, the benefit of having this deeply functional flexible platform is that Vena could say yes to almost any part of the market.

A good path to the CEO’s spot [9:23]

Sam Jacobs: Is commercial leadership a good path to a CEO?

Hunter Madeley: When I first got into sales, it was simply because I was working really hard at a job that paid me the exact same amount no matter how hard I worked. A friend of mine happened to be smart enough to see something in me that I didn’t probably see in myself and said, “Hey, listen, I worked for this great company called ADP. The commissions I earned last quarter are more than you make in a year. Why don’t you come and try to get a job here?”

I got in and I realized this is exactly for me because I’m a pretty maniacally goal-oriented guy. I always loved being a part of the team.

I loved my time as a manager, moved into the frontline manager, and I was fortunate enough to get tapped on the shoulder to move into the director and then VP roles. So, I worked my way up the go-to-market side of the engine.

You get this real well-rounded view of what’s actually happening in the market.

Surprises in the top job [17:32]

Sam Jacobs: Is there anything surprising about the CEO job? When you think about the most difficult part of the job, what stands out?

Hunter Madeley: A big part of my job is determining how we ensure a voice and gather the data and the perspective, and then come to terms on how we’re going to align and move forward. The solution is never a reflection of a single person’s view on how it’s best to move forward.

The amount of energy I apply in my job to understanding points of view and perspectives and helping coordinate the appropriate response and gaining alignment has been both the most exhausting and rewarding parts of the job.

I underestimated how much of my job would be just about alignment and getting people moving forward together.

Hunter on lessons learned during COVID [19:19]

Sam Jacobs: Halfway into your tenure we got hit by a global pandemic. How did the company respond? How did you respond? Tell us about lessons learned over the last 12 months.

Hunter Madeley: There’s a bunch of companies that really benefited. Those companies had all sorts of interesting investment decisions to manage growth. Others got really hurt because their industry got crushed. We were in the middle.

What’s happened over the last year didn’t particularly help us or hurt us in the moment, but our ability to react to it and adjust to it mattered.

As you can imagine, we have a lot of tools and a point of view on how to be agile. As a leadership team, we took a look at our assumptions of our funnel, the market, and how demand was going to be affected. We did our best to soften expectations for a few quarters.

What we really didn’t want to do though is back off our selling or our servicing resources, because we really felt that after two to three quarters, we’d be back in a position to keep growing the company really fast.

The keys to successful agile planning [23:16]

Sam Jacobs: What are the keys to successful agile planning? What is the principal philosophy that underlies the software that your customers use?

Hunter Madeley: There’s some resilience in the original way businesses built themselves. They set budgets, targets, and plans. Part of the value of a strong leadership team was the ability to execute against this longer-ranged plan.

What we’re seeing now is that part of the reason folks leaned into those long-range plans is they just didn’t have the data, the tools, and access to the data, nor even a point of view on what type of data should be viewed quickly and consistently and repeatedly, so that you can make better near-term decisions.

The gold star for senior leadership isn’t that you built a plan that carried you through 12 months and you hit it exactly. That’s unrealistic in the way the world is shifting and changing. The gold star now is how quickly you adapt and how fluidly you can shift plans and resources to a new market if you see an opportunity.

Sam Jacobs: If you’re in e-commerce, it’s transactional daily volume reporting. At its core, is it really just about accurate cash management?

Hunter Madeley: Accurate cash management is important. Especially if you’re a startup and scale up, you have to keep an eye on that. But as you think about all the leading indicators, it’s literally taking context from product usage data, health indicators of how the product is being adopted and used. It could be marketing and content engagement. It could be lead conversion rates, but it’s this idea that you’ve actually got a set of core metrics that you know serve as healthy proxies for the trajectory of the business and the health of your customer base and the health of your sales funnel on your marketing funnel.

Sam Jacobs: If folks want to reach out, what’s your preferred way for listeners to contact you or the company?

Hunter Madeley: You can come straight to me through LinkedIn. I’m pretty easy to find. I’m literally the only Hunter Madeley on LinkedIn. Or you can just come directly to my email, which is hmadeley@venacorp.com.

Sam’s Corner [34:47]

Sam Jacobs: Hey everybody, it’s Sam’s Corner. Really enjoyed that conversation with Hunter Madeley. One of the things I liked is how he said his career is the perfect background to becoming a CEO. Hunter has a go-to-market background, a sales background, and a marketing background, and he spent years cultivating and developing his expertise. I love to hear that both because I have a background in sales and because there are other points of view out there that the CFO route is the way to become a CEO.

Don’t miss episode #149!

I want to thank our sponsor Outreach. Outreach helps sales organizations turn people into happy customers that pay them money. To see how they do it, how they use the leading sales engagement platform, go to outreach.io/onoutreach.

Once again, thank you for listening to the Sales Hacker podcast. To help us get this in front of more eyes and ears, please leave us a shining five-star review.

If you want to find me, you can connect at linkedin.com/in/samfjacobs or email me at sam@revenuecollective.com. Thanks again to Outreach, and make sure you go to Sales Hacker and become part of their community.

Thanks folks. I’ll talk to you next time.

New Report