In this episode of the Sales Hacker Podcast, we have Tom Glason, co-founder & CEO at Scalewise, a platform that provides scale ups with flexible access to world-class revenue expertise. Join us for an insightful conversation on lessons from over 20 years in B2B sales tech and how to support teams and leaders in achieving their professional potential.
If you missed episode #182, check it out here: Build a Sales Team from the Ground Up with Michelle Pietsch
What You’ll Learn
- How to take control of your career by doing due diligence
- Telling your sales team to set their own targets
- The role of autonomy, mastery, and purpose in motivating people
- The biggest mistakes early stage venture-backed companies make
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Show Agenda and Timestamps
- About Tom Glason & Scalewise [4:15]
- Mistakes of early stage companies [7:50]
- A deep dive into Tom’s career of leadership [10:06]
- Why you should do due diligence before joining [20:28]
- Should reps set their own targets? Yes [25:51]
- Paying it forward [31:05]
- Sam’s Corner [33:27]
About Tom Glason & Scalewise [4:15]
Sam Jacobs: We’re excited to have Tom Glason this week. He’s the co-founder and CEO of a company called Scalewise, which provides coaching resources and fractional support to companies that are going through hyper growth. He’s also the founder of the London chapter of Pavilion. He calls himself a leadership geek and he really is. He’s got frameworks out the wazoo, and is a student of the game as much as he is a leader. Get out your notebook because he drops nuggets left and right.
First, we want to thank our sponsors. Outreach is a longtime sponsor of the show. Their annual event Unleashed Summit is back. Get more details and save your spot at summit.outreach.io.
We’re also sponsored by Pavilion, the key to getting more out of your career. Our private membership gives you access to thousands of like-minded peers, Pavilion University, and over 1,000 workbooks, scripts, and playbooks to accelerate your development. Unlock the career of your dreams by applying today at joinpavilion.com.
Finally Demostack. The product demo is make or break for your deal, but tailoring the story is tedious work. You can edit data and charts with a point and click, and show product stories that win deals faster. See how world class sales works use Demostack to accelerate revenue at demosstack.com.
Tom, welcome to the show. In your words, who and what is Scalewise?
Tom Glason: I’ve spoken to hundreds of revenue leaders and I realized two things. The first one was that we have exceptional talent in Pavilion, experienced revenue leaders who could be really useful to startups who lack the right scaling expertise. I wanted to find a way to help more companies scale the right way. There’s certainly a lot out there that don’t do it right, struggle, and hit some serious bumps in the road.
The second thing I realized was that there were a ton of revenue leaders who wanted to step off the full-time employment hamster wheel and build a more flexible portfolio career, rather than putting in these crazy hours into a startup with poor job security. We all know how tenuous the role of a revenue leader is now. I saw that there were all these really experienced revenue leaders who wanted to advise, coach, consult, or build a fractional career, which gives them more flexibility and less stress than being a full-time employee.
It’s daunting to give up a salary and go and find enough work, and balance business development, and contracts, and invoicing, and payments, etc. We created Scalewise to give startups and scale ups access to world class revenue expertise to help them accelerate growth. From a few hours a month of scale coaching from an experienced leader, through providing them with a fractional leader, such as a really good CMO or VP sales who works two to three days a week. We take care of business development, contracts, and invoicing on behalf of those experts so that they don’t have to worry about that.
It’s been really satisfying to support folks in taking that step out of employment, and they genuinely like sharing their knowledge and being useful. It’s also been great helping startups plug leadership or expertise gaps so they don’t make some of those costly, avoidable mistakes that are so often made when scaling.
Mistakes of early stage companies [7:50]
Tom Glason: We commissioned a report on the scaling journey between series A and B. Not many companies make it successfully through that without hiring the wrong revenue leader, and it’s not that the revenue leader isn’t good, it’s timing, it’s fit, and it’s setting them up for success. Typically, an early stage startup between series A and B goes through two revenue leaders during that period.
That’s a massive waste of time and energy for everyone involved. How can we prevent that from happening? You can imagine the challenges, from how do we build an effective SDR team and get them producing predictable pipeline to how do we build our first CSM playbook and drive upsell, cross sell, and retention. On the marketing side, we get a ton of different briefs from heads of marketing that are struggling to scale the business. We’re really pleased that we can come in and provide scale coaching until an experienced CMO comes in, works with that head of marketing, and enables them to level up.
We all know how challenging it is to hire in the current market at the moment.
A deep dive into Tom’s career of leadership [10:06]
Tom Glason: Selling has been in my blood from a young age. I got my first sales job when I turned 16. A window retailer near me was allowing 16 year olds to make cold calls in a commission only role. I was offered the job on the spot, but being told that if I didn’t book at least one appointment each shift, then I would be fired. Most people got fired after their first shift.
I managed to break the record for the most appointments ever booked in a shift on my first day.
I definitely got the bug for sales. I ended up doing really well.
I joined an early stage company, and we were battling hard to get product market fit. We managed to secure a few paying clients, one of which oddly was the Las Vegas Monorail, but my CEO was spending money like he was Mark Zuckerberg, just pissing money up the wall. I was having a great time, but the burn rate was too high. We ended up flaming out. It was a huge lesson for me in how not to scale a startup.
I ended up working for the worst boss you could ever imagine, who completely ruined my mental health. I won’t go into details, but she was that stereotypical kind of micromanaging, untrusting, brutal bully who crushed my confidence and it impacted my relationships outside of work, my sleep, my self worth. It was awful. I don’t know how I lasted, but I don’t give up that easily.
I never wanted to work in a large corporation again. I hated the bullshit and politics. I wanted to be a leader who has a real positive impact. I wanted to be a leader that was the complete opposite to that awful one. I joined Brightpearl in 2010, after they raised their series A, and spent five amazing years as VP sales and SVP global sales and marketing. I was determined to be the best leader I could be. I read tons of books and blogs, I listened to podcasts, and I worked to build connections with peers that I could learn from.
I stumbled across the Sales Hacker Podcast hosted by the founder of the New York Revenue Collective, exactly what I was hoping to build in London. I sent you a LinkedIn message asking if I could pick your brains, we met for lunch, and we both had the same vision about how useful leaders could be to one another. Soon after that, London became the second chapter. It’s incredible to see 5,000 members globally and an incredible membership offering, events, career services, structured learning programs, mentoring resources, and more. I have a huge amount to be grateful for as I don’t think I would’ve founded Scalewise if it wasn’t for Pavilion. Thanks again, Sam!
Why you should do due diligence before joining [20:28]
Tom Glason: When you’re joining at series A stage, you accept that there’s an element of risk around things like market fit and scalability. I certainly wish I’d done more DD with a couple of companies I joined, although there was one that I thought I’d got the DD right, and it ended up being a disaster.
I believe that regardless of what role you are going into, you are taking a leadership role.
Should reps set their own targets? Yes [25:51]
Tom Glason: We have a duty to our teams to recognize what motivates each individual and to tap into this rather than using targets as a blunt instrument to drive performance. As humans, when we have something imposed on us, it takes away our autonomy. Dan Pink’s great book Drive references it as one of the three things, autonomy, mastery, and purpose, that really drives happiness at work and engagement. The happier people are, the more productive they’re going to be.
Paying it forward [31:05]
Tom Glason: This is the beauty of being in Pavilion, I can reel off so many names of people that have had an impact on me in one way or another. Pete Crosby is actually a good friend of mine now, but when I was building the chapter in London he was so pivotal. Laura Kightlinger on the customer success side, exceptional CS leader, Hannah Godfrey, and Rob Whiteside. There’s a ton of folks to be honest, Sam, and this is why Pavilion has been life changing. I’ve met so many great people.
You can get me on LinkedIn. LinkedIn.com/TomGlason, or you can send me an email at Tom@scalewise.com.
Sam’s Corner [33:27]
Sam Jacobs: Tom has built an impressive and exciting company called Scalewise that’s got global expansion plans. He’s been doing sales leadership for 20 years. He dropped a lot of nuggets that I thought were really interesting.
The first is due diligence is so important. He talked about some of the fits and starts with terrible bosses and with founders that were fighting each other. The trick here is doing your research and doing your homework. You need to do the work on backchannel references, you need to have a fully formed understanding. And even then, it still might go wrong.
The second big idea was where he removed targets. He said to the team, “You make your own targets.” Here’s what the requirements of the job are, here’s what the business needs to go. Within that framework, you take control, you tell us how you want to be held accountable. You want to feel like the decisions that you make in your life are your own. Consider removing quotas and having your reps choose their quotas. A pretty radical innovation that I thought was really interesting.
Before we go, we want to thank our sponsors:
- Outreach – go to summit.outreach.io
- Pavilion – unlock the career of your dreams joinpavilion.com
- Demostack – accelerate revenue at demostack.com
If you want to get in touch with me you can: Sam@joinpavillion.com or on LinkedIn. I’ll talk to you next time. Thanks for listening.
