Fireside Friday with Paul Rosen
Updated: Feb 28
Sales Assembly: Give us your quick background in sales.
Will: From 2011-2017, I was the Chief Sales Officer for On Deck and grew the team from 15 to 250 and revenues from $10M to $350M over that period of time. Currently, I'm the Chief Revenue Officer for ShipBob. We have grown the AE/BDR team from 40 to almost 70 over the last 60 days.
Sales Assembly: What's your biggest accomplishment in sales or sales leadership?
Paul: My biggest accomplishment was the On Deck IPO in December of 2014. At the time, it had a $1.4B valuation ($60M valuation during the C round in 2011).
Sales Assembly: What's the best piece of sales advice you ever got?
Paul: "A's" hire "A's," and "B's" hire "C's." An "A" will hire people who are better, smarter, and more efficient than they are. An "A" realizes that the only way to win in a competitive environment is to hire great people. "A's" are not self-conscious and are more worried about getting the job done vs who gets the credit. An "A" will always want to work for/with another "A." A "B" will worry about their team members outshining them and losing their position, authority and/or influence. So they will tend to hire "C's," which is very dangerous if you are expecting growth and strong levels of productivity.
Sales Assembly: What's the biggest challenge facing a sales rep today, and how would you recommend they overcome it?
Paul: Increase in information and competition. It is becoming more difficult to differentiate yourself. I would do things that you don't get paid for to become a valued resource. If you add value, the business will come.
Sales Assembly: Do you currently have a mentor, or have you ever? If so, what did they teach you?
Paul: One of the best ways to grow and develop is by having a strong mentor. I haven't had one recently specifically to sales, but Noah Breslow, our CEO at On Deck, was a great mentor professionally. His advice was to always have an "N2" or a number 2 (someone who can replace the work that you are doing today). As you are scaling, it is important to determine if you have the talent internally to develop into N2's (which is ideal), or if you have to hire outside. Either way, if you don't have an N2, you will get stretched too thin and limit your overall growth. He also helped me press a little before hiring someone. He told me "If there is any doubt, there is no doubt" (don't hire him/her).
Sales Assembly: What's the best sales book you've ever read? What are you reading now?
Paul: Best- Brian Tracy- Goal Setting. Current- Predictable Revenue by Aaron Ross
Sales Assembly: Best sales or business related books, articles, podcasts or newsletters?
Paul: Jeffrey Gitomer - Blog, E-zine | Gary V - Podcasts | Brian Tracy - Really impactful book, Goals.
Sales Assembly: What's the best advice you'd give to someone just starting a career in sales?
Paul: Whatever is asked of you, do 20% more.
Sales Assembly: Do you see any interesting future trends as it pertains to sales?
Paul: Importance of the sales ops function, continued migration to inside sales and evolution of the BDR/AE model. Twenty years ago, sales results were less predictable, most industries utilized outside salespeople, and salespeople were responsible for hunting leads, as well as selling them. Within the last 5-10 years, companies have really started investing in sales ops and enablement departments to help "Moneyball" the business. What I mean by this is using data, reporting and tools to optimize and find needle movers/levers to grow. Examples could include finding leaks in the funnel, how to re-engage in older leads, contesting/gamification and implementing new technology to more efficiently contact customers. Many B2B sales (even larger, more enterprise types of sales) are now conducted over the phone. Often times, a company will have a BDR (Business Development Representative or Sales Development Representative), who is a junior sales person, responsible for engaging with new customers, qualifying and then lobbing the lead over to the AE (Account Executive) to sell. This model works well in industries that are either higher margin or where customers generate $10K or more per year in revenues. The BDR/AE is a nice way to have an immediate career path for a newer salesperson. The natural progressions, at an AE level, can be A) Management/leadership, B) Becoming a subject matter expert and crushing it in enterprise sales (and making a lot of money) or C) Migrating to sales ops (if you are a little more analytical) and finding ways for the entire team to run better.
Sales Assembly: When was the biggest failure that you have had, and what did you learn from it?
Paul: I started a company with two other guys many years back. We grew revenues quickly, but we drove the business into the ground financially and operationally. The biggest takeaway was to focus on the stuff that you are good at and enjoy and find people to take care of your blind spots.