Finding the Perfect Fit—Managing and Hiring in the New Sales World with Mike Sadler

In this episode of the Sales Hacker Podcast, we have Mike Sadler, SVP Americas at Similarweb, the must-have platform for effective online marketing. Join us for a lively conversation about managing, hiring, and beating the recession.

If you missed episode 215, check it out here: Why Champion Lifetime Value is Critical with Christian Kletzl

What You’ll Learn

  • The biggest job in any sales organization is the frontline managers who do the training
  • How you become a manager of managers
  • Overcoming hiring challenges and doing great discovery
  • Recession-proofing your reps

Subscribe to the Sales Hacker Podcast

Show Agenda and Timestamps

  1. About Mike Sadler and Similarweb [03:01]
  2. Avoiding mistakes and scaling your leadership approach appropriately [06:41]
  3. Building the perfect hiring profile [10:14]
  4. Selling in a down economy and making your team recession-proof [14:54]
  5. How selling has changed in the past 20 years [17:25]
  6. The changing role of salespeople [20:26]
  7. Paying it forward [21:47]
  8. Sam’s Corner [23:10]

About Mike Sadler & Similarweb [03:01]

Sam Jacobs: Welcome to the Sales Hacker podcast. Today on the show, we’ve got Mike Webb. He’s the SVP and GM of the Americas for a great company called Similarweb. They do a bunch of cool stuff just around helping you understand how your company or website is performing relative to the market, relative to competitors. Really important, critical information that you probably need, particularly in an economic environment, such as the one that we’re in. So it’s a great conversation.

Now, before we bring you this conversation, we want to thank our sponsors. Our first sponsor is Conga. Businesses run on documents, Conga is changing the way the world works by modernizing, streamlining, and automating your documents, contracts, and processes to make it easier to do business. See why Conga is the number one paid app on the Salesforce app exchange with a free trial or demo today at

Our second sponsor is Outreach, the number one sales engagement platform. Outreach revolutionizes customer engagement by moving away from solid conversations to a streamlined and customer centric journey. Leveraging the next generation of artificial intelligence, the platform allows sales reps to deliver consistent, relevant, and responsible communication for each prospect every time, enabling personalization at scale previously unthinkable. Check out for more information.

And finally, we just turned into a community. Rather than just reading or listening, you can now ask questions and get amazing thoughtful answers from the world’s B2B sales professionals who’ve been there before, plus you can share your experience with others. Go to and create your profile today.

Now, without further ado, let’s listen to this interview with Mike Sadler.

Sam Jacobs: Today on the show, we’ve got Mike Sadler. Mike’s the SVP and GM Americas at Similarweb and is responsible for leading and growing the revenue organization for North America and Latin America. Before Similarweb, Mike held multiple go-to-market leadership positions at Everbridge and Gomez Inc., now doing business is Dynatrace. During their growth phases, from 10 million in ARR startups to an IPO in the successful acquisition, respectively. Mike attended Colgate University of New York, where he graduated cum laude with a bachelor’s degree in sociology. He’s been a Pavilion member since it was still called Revenue Collective back in 2019. Mike, welcome to the show. Tell us about the company. What do you all do?

Mike Sadler: The vision of Similarweb is to be the digital measure of the internet, which can mean many different things. If we break it down into what it means for our customers, our primary business or our historical business has really been focused on helping digital marketers and consumer insights teams to understand what’s happening outside of the black box they can see. Most companies these days use Google Analytics or Adobe analytics to understand where their traffic’s coming from, how long people are staying on the site, and what their bounce rates are. But looking at it through a competitive lens is very difficult, understanding how that compares relative to competitors or what best practices they’re using. We really help shine the light on that.

Avoiding mistakes and scaling your leadership approach appropriately [06:41]

Sam Jacobs: What do you think made you successful, and what do you see other people do that makes them unsuccessful?

Mike Sadler: What made me successful was having some really good mentors and leaders to go to and being maniacal about learning from my mistakes and not repeating them. I’m a big fan of the Albert Einstein quote, “Doing the same thing multiple times expecting different results is the definition of insanity.” So I really tried to learn from that. The biggest mistake I’ve seen people make, and I’m definitely guilty of doing this when I first moved into the team lead role, is just trying to be a super rep by trying to take on too much and not allowing their team to grow under them.

Building the perfect hiring profile [10:14]

Sam Jacobs: Do you have a hiring profile that you look for? Is it pretty standard in terms of the types of people that you think will make great reps or great managers? Hiring in sales is probabilistic, and sometimes people interview really well, but interviewing really well isn’t quite the same thing as being great at discovery or great at closing. So, how do you think about the hiring profile, hiring process, and building the team?

Mike Sadler: I’ve hired some great people, and I’ve hired some people that probably weren’t the right fit. The one thing every salesperson can sell is themselves, even if they can’t sell your product. You have to be really clever. What I’ve tried to do is come up with a set of questions I use consistently that are a little bit tricky. I hesitate to share some of those questions.

But, there are a couple that I can share. I’ll shout out to a really strong sales leader in the Boston area, Josh Allen, who shared a framework I use today with me. It includes breaking down a set of hiring criteria into four areas: knowledge, skills, characteristics, and experience.

So, knowledge would be industry knowledge or awareness of the market. Skills are the skills that are specific to the role. Experience is a track record of success in a similar company and deals size. The characteristics include those intangibles, the grit, curiosity, and intelligence that people look for. I work with my leaders to map out what works along those four quadrants and find the ones that are nice to have and non-negotiables. Then, we try to design the interview questions based on that.

Selling in a down economy and making your team recession-proof [14:54]

Sam Jacobs: Changing the subject slightly, maybe we’re in a recession, maybe we’re not. Certainly, indicators are that we are in a very different economic environment. How are you thinking about working with your teams to respond to this environment? What’s your perspective on it?

Mike Sadler: We did a training a few weeks ago on selling in a bit of a down economy with a group. I remember reading an article a while back that said the best salespeople are recession-proof, and I believe that. Generally, companies with good product-market and go-to-market fit will be aligned to one of the three things you can sell: improving revenue, reducing cost, and reducing risk. People that can succeed in tough economic times tend to be good at pivoting a message to align well with one of those components.

How selling has changed in the past 20 years [17:25]

Sam Jacobs: Do you think selling has changed over the last 20 years?

Mike Sadler: Tactics change. I don’t think there’s ever going to be a point where good selling gets away from discovery. The bigger fundamental shift was probably longer ago with the advent of the internet and B2B websites. There was a time when you couldn’t just go on the internet and find 80% of everything you needed to know. You had to call a salesperson to find out information about a product. That was a titanic shift in selling.

There are technologies out there that have provided the possibility to make things more efficient. But to me, the core fundamentals are still around discovery and qualification.

The changing role of salespeople [20:26]

Sam Jacobs: Do you see things changing over the next couple of years? Product-led growth, do you see that changing the role of salespeople, or does it just make it even more important? How do you think about low-cost acquisition models for building out a large B2B sales team?

Mike Sadler: Product-led growth has been around for a while, but it’s gotten a lot more attention in the last couple of years. I think it’s a great source of leads if you can do it. It’s really important to have the discipline within those sales teams that try to convert inbound leads or self-signups into larger customers. They need to be discovery focused, and I think that gets missed. People assume an SMB sale is transactional and not a complex sale. Having led both inside and enterprise teams, I can tell you that for some products, SMB sales are just as complex as at the enterprise level.

Paying it forward [21:47]

Sam Jacobs: I think you’re right, Mike. We’re almost at the end of our time together. What we like to do towards the end is sort of pay it forward and talk about some of the people, books, content, trainers, founders, and investors that have made a big impact on you that you think we should know about. You already mentioned our mutual friend, Josh Allen, but who else comes to mind when you think about people we should know about, maybe people we should have as guests on the Sales Hacker podcast?

Mike Sadler: I think a good guest would be a guy named Mike Myers from Sandler Institute. He had a franchise that focused almost exclusively on SaaS companies and did well. I was fortunate early in my career to have him come in and do some training for us. His franchise ended up getting acquired by Sandler because they were doing such a good job winning all the SaaS business. But he’s awesome, so I’d definitely recommend him if you haven’t already spoken to him.

Sam’s Corner [23:10]

Sam Jacobs: Hey, folks. Sam’s corner. I really like that conversation with Mike Sadler. Classic Northeastern, Boston sales leader in the vein of exactly the guy that he mentioned, Josh Allen, who clearly has a ton of intelligence and insight around how to build an effective team. Mike wouldn’t have had the outcomes he’s had if he wasn’t great at his job but still approachable and not somebody pie in the sky, sitting in an ivory tower. He’s capable of leading from the front, closing big deals, and empowering and training the trainer. He mentioned that the single biggest job in any large sales organization is the frontline sales manager, who is training the reps daily.

So the challenge as you grow and become a larger organization is how do you influence the trainers and managers? How do you become a great manager of managers? Part of it is the process, part is inspiration and vision, and part is making sure you’ve hired the right people.


Give us five stars on iTunes or Spotify or wherever you get your podcasts. Join the Sales Hacker community. Get any question answered. Go to and join 20,000 people answering questions and offering support and help.

Reach me at and I’ll talk to you next time

Join Us Today

Insider access to the GTM network and the best minds in tech.

Join Us Today

Insider access to the GTM network and the best minds in tech.

Trending Now

You may also like...