Fireside Friday with Jeff Pearlman
Sales Assembly: Give us your quick background in sales.
Jeff: I moved into sales leadership at Groupon following 3.5 years there as an individual contributor. I worked in our on-boarding department, where I got to learn about both management and training which was a great experience and helped propel me into sales leadership roles at other tech companies. Following a couple of years at Hireology, I made the move to ReviewTrackers to lead their sales organization.
Sales Assembly: What's your biggest accomplishment in sales or sales leadership?
Jeff: In 2018, when I got to ReviewTrackers, we were going through a transition, and many of the tenured sales reps had left or were on their way out. It was a challenge having to rebuild the team in my first year, while also learning the product and implementing new systems/processes. At the end of the year, we were able to hit our number despite all the challenges. This was a win I am very proud of.
Sales Assembly: What's the best piece of sales advice you ever got?
Jeff: In one of my first months at Groupon, we were going through our S1, and things were pretty crazy - long nights, weekends in the office, new rules and comp plans, etc. A lot of people were frustrated and complaining or challenging managers on what they were doing. Our RVP at the time had a meeting with our region, and I remember him saying that it was ok to challenge things if you think they are broken. If you stop challenging what needs to be fixed, it typically means you have given up. I try to use this advice as I build new processes, ask managers to poke holes in anything we are rolling out and when speaking to reps about issues/concerns they have.
Sales Assembly: What's the biggest challenge facing a sales rep today, and how would you recommend they overcome it?
Jeff: Buyers have the info they need at their fingertips. They can go online and research you and your competitors before ever taking a call. They can learn about most things you are trying to sell them on without needing to talk to you. To overcome this, you need a compelling value prop to get people to take a meeting. For example, we arm our reps with tools, so that a prospect truly sees the need to take a meeting with us. Instead of a generic product demo, we demo prospects with their own real business data so that before they even buy from us, they can take actionable steps to improve their business based on what they heard on the call. We also arm SDRs with tools to give a prospect real insights into their own business through a prospecting email by using our proprietary scorecards. None of this would be possible if we did not have interdepartmental communication. Our product and engineering teams built these tools for us, because they saw the need. So to summarize, work with other departments to find a way to differentiate yourself beyond just using a subject line that references where someone went to college or what team they are a fan of. Provide real value.
Sales Assembly: Do you currently have a mentor when it comes to sales, or have you ever? If so, what did they teach you?
Jeff: I was fortunate to start in management with a great team around me at Groupon. Many of those folks are now part of Sales Assembly, and I look at them as both peers and mentors. Max Lowenbaum stands out as he gave me my start in sales leadership, and I had the pleasure of working under him at two companies where I learned a lot about process building and scaling.
Sales Assembly: What's the best sales book you've ever read? What are you reading now?
Jeff: The Challenger Sale was the book that really clicked with me when I was starting in sales. Currently, I am reading The Transparency Sale.
Sales Assembly: Best sales or business related articles, podcasts or newsletters?
Jeff: As I have been reading The Transparency Sale, I have now subscribed to Todd Caponi's blogs and am finding them very useful. I also like listening to Gary V - good motivator.
Sales Assembly: What's the best advice you'd give to someone just starting a career in sales?
Jeff: Make a name for yourself. Look at what others in your role are doing in terms of activity and do more. Find the people in your role having success and learn from them. Work hard and smart.
Sales Assembly: Do you see any interesting future trends as it pertains to sales?
Jeff: As noted above about challenges salespeople are facing, buyers are more educated than ever. This means salespeople need to evolve, and the stuff that worked for Grant Cardone and Jordan Belfort may not work for salespeople today.
Sales Assembly: What do you look for when hiring sales reps?
Jeff: I look for people who are curious, coachable, autonomous and resourceful. Those are all key characteristics, but I also look for people who are truly driven by career growth and money. Most people will say in an interview that those two things drive them, but it is not always the case. The systems in place at my sales org are designed to reward the overachievers - both through promotions and commission accelerators. If you are really driven by those things, then you typically do well on the team. If you aren't, that is ok, but it may not be the best fit.