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Matt Rosenberg: Why You Should Not Hire Sales Leaders From Big Companies | E1068

Matt Rosenberg is Grammarly’s Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite’s CRO leading them to become the largest event platform in the world by event count. ---------------------------------------------- Timestamps: (0:00) Matt Rosenberg’s Journey to CRO of Grammarly (6:55) How to Build and Impliment a Sales Playbook (12:42) Best Tips on Hiring for Sales (23:24) How to Do Sales DIscovery (33:00) How to Do Discounting (38:34) Story of Joining Grammarly & How to Prospect for Talent (42:12) How to Expand Your Customers (47:50) Quick-Fire Round ---------------------------------------------- In Today’s Episode with Matt Rosenberg We Discuss: 1. From Miserable Lawyer to World Beating Sales Leader: How did Matt make the transition from lawyer to sales leader? What does Matt know now that he wishes he had known when he started in sales? What are Matt’s biggest pieces of advice for anyone who wants to make a career change and is lacking confidence? 2. The Playbook and Hiring The Team: How does Matt define the “sales playbook”? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire? 3. Discounting, Champions and Urgency: What can sales team do to create urgency in deal cycles? What works? What does not? How does Matt approach discounting? When to do it vs when not to? What level is acceptable? What are the biggest secrets to creating champions within prospects? Why does Matt believe that deals are won and lost in prospecting? 4. Developing Great Sales Talent: How does Matt use sales call recordings to train teams? What is his 3×3 matrix for coaching calls? What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews? What are the single biggest elements sales leaders can do to nurture sales talent? What are the biggest mistakes sales leaders make when developing talent internally? ---------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ---------------------------------------------------------- #MattRosenberg #grammarly #HarryStebbings #venturecapital

Matt RosenbergguestHarry Stebbingshost
Oct 3, 202351mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Why Big-Company Sales Leaders Fail Startups, And Who To Hire Instead

  1. Matt Rosenberg, CRO of Grammarly, shares how his unconventional path from law to early-stage startups shaped his views on sales leadership, playbooks, and hiring. He argues that most founders overvalue big-company pedigrees and pre-baked playbooks, and undervalue analytical generalists who can actively listen, learn markets, and build from zero. Rosenberg emphasizes flexible, data-driven sales processes, deep discovery, and tight collaboration in the earliest sales hires to create momentum and real product–market fit. He also breaks down how to move from PLG to enterprise, where to place incentives, and why more women (especially parents) should be in sales leadership.

IDEAS WORTH REMEMBERING

5 ideas

Don’t import rigid playbooks; build the critical 20% in-market.

Rosenberg argues that while 80% of sales process is transferable, the winning 20% is company- and market-specific, discovered only after you’re “punched in the face” by real customers and iterating in the field.

Hire flexible, analytical first sales leaders—not ex-Google logos.

He cautions founders against over-indexing on big-brand pedigrees and instead recommends ex-bankers, consultants, or lawyers who are strong active listeners, pattern-finders, and critical thinkers able to define ICP, messaging, and motion from scratch.

Start with a sales leader plus rev ops, then hire in collaborative pairs.

Rosenberg prefers starting with a senior seller who can scale and pairing them quickly with strong sales/rev ops to codify process, then hiring two reps at a time to maximize shared learning, not internal competition.

Great discovery wins deals fast; bad discovery leads to slow losses.

Effective discovery begins with research, then explores priorities, success metrics, what’s working, what’s not, and—crucially—the impact of solving those problems, which later powers urgency, pricing discipline, and shorter cycles.

Create urgency by quantifying economic impact, not by gimmicks.

If you can tie your solution to hard financial outcomes and agree on the value of delay, you can frame slippage as real cost and move customers (and CFOs) to act, especially for painkiller products.

WORDS WORTH SAVING

5 quotes

Deals are won and lost in discovery. Bad discovery leads to very long losses; good discovery leads to very quick wins.

— Matt Rosenberg

Don’t hire anybody that says on their LinkedIn, ex-Google, ex-Amazon, ex-Facebook.

— Matt Rosenberg

Everybody has a plan until they get punched in the face. When you get into the market and start to get punched, you then develop your playbook.

— Matt Rosenberg

If you really want to find a great sales executive, hire a mom.

— Matt Rosenberg

Founders have superpowers in lots of areas, but my point of view is building a playbook ain’t one of them.

— Matt Rosenberg

Career pivots from traditional professions (law) into startup sales leadershipBuilding momentum and confidence in early-stage sales teamsSales playbooks: what’s reusable vs. what must be custom-builtHiring first sales leaders: profiles, seniority, and why not to hire big-tech pedigreesDiscovery, urgency creation, and selling to CFOs in tough budget environmentsUsing data and sales/rev ops to shape process, coaching, and prospectingTransitioning from PLG/consumer to enterprise motion and designing incentives

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