• Sales Assembly

Fireside Friday with Robert Merritt

This is our interview with Robert Merritt, VP of Enterprise Sales at Upwork. You can follow Upwork at @Upwork.

Sales Assembly: Give us your quick background in sales.

Robert: My background consists of 16 years in the talent/human capital industry. I cut my sales teeth at Careerbuilder.com in the early 2000s and caught the entrepreneurial bug at age 26 when I started a sales and marketing recruiting firm. I owned and operated that business for seven years and after a brief stint in the executive search field, I made my way to Upwork. Over the last three years, I've had the life-changing opportunity and experience to be a key contributor on the team of executives who are building Upwork's Chicago presence and enterprise business.

Sales Assembly: What's your biggest accomplishment in sales or sales leadership?

Robert: I don't really ever think of accomplishments or failures. I probably sound like a total flake, but I've just always looked at it like a series of highs, lows and learning experiences that have made me the confident, growth-focused leader and business professional I am today.

Sales Assembly: What's the best piece of sales advice you ever got?

Robert: "It's not the customer's job to figure this shit out." - Bob Montgomery, Former CEO and Chairman of Careerbuilder.com (when they still called it .com)

Interpretation: As Sales Professionals, it's our job, not the customer's job, to find the right opportunities and problems to solve, be prescriptive, add value and never give up in our efforts to make sure the customer's experiences are world-class and that their expectations are exceeded.

Sales Assembly: What's the biggest challenge facing a sales rep today, and how would you recommend they overcome it?

Robert: Challenge: Living under the delusion that selling is supposed to be easy and that customers are actually interested in what you have to say.


1. Get your mind right and expect success to be hard.

2. Read, research, prep and work harder than everyone else at knowing your customer, their business and their problems so that you're prepared with something meaningful to say when you finally have the opportunity to make that impression.

3. Persistence, Persistence, Persistence. Never stop trying to add personal value. It's really hard to say no to a person who genuinely wants to make a positive impact on your business and is committed to the long and painful process of establishing credibility and earning your business.

Sales Assembly: Do you currently have a mentor when it comes to sales, or have you ever? If so, what did they teach you?

Robert: I've had two mentors: Bob Montgomery, former CEO of Careerbuilder, and, my current boss, Eric Gilpin. These two individuals have taught me too many things to be cited. I'll just say their mentorship and perspectives have shaped and continue to shape who I am as a sales professional, leader and person.

Sales Assembly: What's the best sales book you've ever read? What are you reading now?

Robert: That's a really hard question. There are so many great sales books out there. What I've learned is that they're all different and yet all the same. A few books I would recommend are: Questions That Sell, Question Behind the Question, Exactly What To Say, Predictable Revenue and Sales Engagement.

Best book I've ever read: Principles by Ray Dalio.

Sales Assembly: Best sales or business related articles, podcasts or newsletters?

Robert: Podcast: "How I Built This." This is an American podcast about "innovators, entrepreneurs, idealists and the stories behind the movements they built" produced by NPR.

Sales Assembly: What's the best advice you'd give to someone just starting a career in sales?

Robert: Two pieces of advice:

1. Start your sales career by living by this credo. "I'm are a professional salesperson. The operative word is "professional." As a professional salesperson, I'm 1) Expected to perform, and if I don't, I expect to be replaced and 2) expected to improve every single day through the rapid application of training and feedback." Live by this, and you'll probably be more successful than 95 percent of the salespeople in this world.

2. READ READ READ APPLY APPLY APPLY and get one percent better every single day. Most salespeople are all too willing to be stagnant and not grow, because it's much easier in the short term.

Sales Assembly: Do you see any interesting future trends as it pertains to sales?

Robert: I like the trend towards more personalization, context and prospecting effectiveness, with less emphasis on call and email volume and cadences.

Sales Assembly: What's your best advice when it comes to hiring sales professionals?

Robert: 1. Set ridiculously clear and candid expectations about what's expected of them in the job.

2. Ask them to commit and agree to these expectations before they're hired. Like a contract.

3. Hire people that you "fall in love with." If you don't love them, don't hire them.


Join thousands of your peers who receive our weekly email with sales insights, news & events.

Find us at 1871

222 W. Merchandise Mart Plaza

Ste. 1212

Chicago, IL 60654


© 2020 by