Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team

My Guest

Dave Prusinksi is the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space.

Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave’s leadership, FleetComplete grew their annual revenues by ~25x, achieving a ~50% revenue CAGR for 9 of his 10 years.

Dave played an integral role in the acquisition of 6 companies, leading the sales and marketing due diligence processes, and ultimately integrating the operations of the acquired businesses into that of FleetComplete. In addition to acquiring and investing in SMBs for FleetComplete, Dave was also a central member of the deal team helping to lead FleetComplete through multiple investment and acquisition rounds themselves, managing the sales & marketing due diligence processes in each instance.

Dave has served as a Revenue Coach to several SMBs, working directly with their CEOs and Heads of Sales to optimize their sales and revenue generation processes. All of the companies with whom Dave has worked thus far have exited with great success.

Prior to FleetComplete, Dave was National Sales Manager at Research in Motion, where he jointly grew one of the company’s largest divisions with $1B+ in annual revenue

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Specific Questions and When They’re Asked

Hiring and Onboarding

(3:50) What are the most common mistakes that CEOs make when hiring a Head of Sales?
(5:40) How do you hire a Head of Sales who can scale while also avoiding “over-hiring” risk?
(7:00) How important is industry experience when hiring individual sales reps?
(9:30) When should a CEO expect a new sales hire to pay for themselves?
(12:00) How do you evaluate new sales hires if your company has very long sales cycles?
(14:25) How do you translate a revenue goal into a quantifiable activity goal for each rep?
(18:40) If building a sales team from scratch, who should you hire the first? Leader or individual contributors?
(22:50) How do you most effectively ramp/onboard newly hired sales reps?
(25:30) Should CEOs utilize their existing reps to help onboard newly hired reps?

Compensation Plans

(27:30) What are the biggest mistakes CEOs make when crafting incentive comp plans?
(30:25) How do you know if a comp plan is sufficiently simple & easy to understand?
(33:40) How do you re-structure a comp plan mid-year if you’re forced to do so?
(35:20) How do you know if you should change a comp plan mid-year vs. leaving it as is?
(39:00) How much change do you generally make to your comp plans year-over-year?
(41:00) When should a new annual comp plan be in the hands of sales reps?

Team Attrition

(42:30) How do you deal with a high performing rep who is a cultural net-negative?
(45:20) How do you deal with with a successful VP of Sales who is on a cold streak?
(48:15) How do you minimize churn of BDRs? Do you have to accept it’s a high churn role?
(50:05) Does sales have to be a high turnover group? What are best practices re: retention?
(52:55) How do leaders deal with reps who are frustrated with things beyond their control?

Functions Supporting the Sales Team

(55:00) How do you make the link between Sales & Marketing as strong as possible?
(59:20) Does external lead gen work? What should you outsource vs keep in house?
(1:01:25) Does product complexity impact the effectiveness of outsourced lead generation?
(1:03:45) What does Sales Ops do, and how do you know if you need Sales Ops or not?
(1:05:05) How do CEOs know when to add various supporting functions to the sales team?

Scaling a Sales Team

(1:07:40) How do you know when it’s time to scale and add significant headcount?

General

(1:11:25) How involved should a CEO be in sales?
(1:13:35) How do you specialize between hunters (AEs) & farmers (AMs) with a small team?
(1:15:50) What 5-10 metrics should be on every CEO’s sales-specific dashboard?
(1:20:15) What resources (books, blogs) that CEOs should familiarize themselves with?
(1:27:45) If you could shout something from the mountaintops that every CEO should know specific to sales, what would that be?