The Twenty Minute VC

Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners. -------------------------------------------------------- Timestamps: 0:00 How did Maggie get into Sales? 4:50 Biggest Lessons from Slack 5:47 Cross-Functional Relationships 10:52 Product-Led Growth 20:31 Outbound Sales 33:50 Net Payment Terms 35:12 Tips for Hiring Salespeople 58:55 How to Choose Which Startup to Work For 1:02:29 Which Sales Tactics are Dead? 1:04:30 Parental Leave 1:06:44 Advice for Sales Leaders 1:07:33 Who has the most impressive sales strategy? -------------------------------------------------------- In Today’s Episode with Maggie Hott We Discuss: 1. The Cold Email that Led to a World-Class Sales Career: How a cold email to Kevin Hartz @ Eventbrite led to Maggie’s career in sales? What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset? What does Maggie know now that she wishes she had known when she entered sales? 2. The Sales Playbook: PLG and Enterprise: How does Maggie define the sales playbook? What is it? What is it not? Is it possible for early-stage companies to do both enterprise and PLG at the same time? When is the right time to add enterprise to a PLG motion? What are the steps to build an outbound sales engine in enterprise? Where do many go wrong? 3. Building the Bench: Hiring Your First Sales Team: Should founders look to hire a Senior Head of Sales first or a more junior sales rep? Should they be hired one at a time? What are the benefits of hiring many at the same time? What is the right process to hire your first sales hire? What are the core traits and habits that make the first 10x sales hire? What are the right questions to ask to unveil those characteristics? 4. Making the Machine Work: The Process: What can sales leaders do to proactively build relationships with other parts of the org? How can more junior sales reps build relationships with other functions? Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound? Why is it dangerous to make your self-serve product too good? -------------------------------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/maggie-hott/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Maggie Hott on Twitter: https://twitter.com/maggie_hott Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok -------------------------------------------------------- #MaggieHott #Webflow #HarryStebbings #salestips

Harry StebbingshostMaggie Hottguest

Dec 14, 20221h 8mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Maggie Hott Reveals How To Hire And Build Elite Sales Teams

Maggie Hott, former top Slack seller and now Director of Sales at Webflow, walks through how she broke into sales and helped scale Slack from $12M to over $1B ARR before building Webflow’s sales org from scratch.
She explains how to introduce sales into PLG companies, why outbound must start early, and how to design product and pricing so self-serve doesn’t cannibalize enterprise revenue.
A major focus is on hiring: who your first sales hires should be, how to structure interviews, the three questions to ask every sales rep, and why you should never have candidates demo your product in a final round.
She also dives into compensation, discounts, parental leave, and concrete tactics for discovery, outbound, and cross‑functional relationship building that actually scale in hypergrowth environments.

IDEAS WORTH REMEMBERING

5 ideas

Don’t hire a Head of Sales first; hire builders who’ve seen early-stage before.

Your first sales hires should be AEs or new managers from hypergrowth companies who have actually built motions and tooling, not big-company VPs who are expensive, far from the work, and need enablement and ops you don’t have yet.

Start outbound immediately and treat it as a brand-building engine, not just pipeline.

Cold outbound rarely lands a deal at the perfect moment; its real value is educating future buyers that you exist so you’re in their consideration set 6–12 months later. This is why delaying outbound, as Slack did, is so costly.

Design clear product differentiation so PLG doesn’t cannibalize enterprise sales.

If self-serve includes too many advanced features, you’ll struggle to sell higher-priced enterprise plans later and you can’t easily take features away. True enterprise offerings need more than SSO—think roles/permissions, legal flexibility, premium support, and advanced security/compliance.

Build for scale early: choose tools and processes for the org you’re becoming.

Buying the cheapest SMB tool and ‘fixing it later’ leads to painful rip-and-replace exercises in hypergrowth. Maggie argues for selecting systems like Salesforce, DocuSign CLM, Clari, etc., earlier than seems necessary so they scale with the team.

Hire for ambiguity tolerance and ability to ‘embrace the chaos.’

Early-stage and hypergrowth sellers must thrive amid constant change—shifting roles, new motions, evolving product. Maggie tests this by asking for concrete examples of handling change and driving process improvements, not just claims of liking “fast-paced” environments.

WORDS WORTH SAVING

5 quotes

There are very few world-class companies that I can think of that don’t have world-class sales teams.

— Maggie Hott

Never, ever wait on outbound.

— Maggie Hott

Choose the company, not the role.

— Maggie Hott

If you make your self-serve product too good, then it cannibalizes your sales team’s revenue, and it’s really hard to go reverse.

— Maggie Hott

A hiring mistake can cost a company to the tune of a million dollars.

— Maggie Hott

Maggie Hott’s non-traditional path into sales and hypergrowth experience at Eventbrite, Slack, and WebflowBuilding sales in PLG companies and avoiding self-serve vs. enterprise product conflictsDesigning and launching effective outbound motions (including PLG-triggered outreach and pure cold outbound)Who to hire as your first sales reps, and why not to start with a Head of SalesHow to structure a rigorous sales hiring process and the key interview questions to askCompensation, discounting, payment terms, and using incentives strategically in dealsSupporting working parents and creating environments where high-performing moms can stay in tech

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