SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC
SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC
Discover how OpenAI's unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at OpenAI, including why they don't pay sales commissions, and what B2B sales leaders can learn from this disruptive model.
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Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026.
With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.
But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait.
Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
Join Maggie Hott, GTM Leader at OpenAI, as she shares her extensive experience in building top-performing sales organizations at SaaStr. With a remarkable career history at Eventbrite, Slack, Webflow, and OpenAI, Maggie distills 15 years of insights into a tactical playbook for building and scaling sales teams. Learn key principles for hiring the right candidates, fostering thriving teams, maintaining customer obsession, and driving sustainable growth. Discover common pitfalls to avoid, the importance of storytelling, and how to align your teams for maximum impact. Whether you're a startup founder or a seasoned leader, these practical lessons will help you scale your sales team effectively. ------------------
Hey everybody, SaaStr AI's next stop takes us to London on December 2nd and 3rd!
It's Christmas with SaaStr and 2,000 of the best SaaS and AI leaders.
The biggest names will be there. The best networking.
Early adopter tickets are selling faster than we expected. So don't wait. With only 5 months until the event, we expect this year's SaaStr London event to sell out to capacity.
Use my code jason20pod for exclusive savings. Get your tickets now at podcast.saastrlondon.com or use code jason20pod at checkout.
SaaStr AI London – where SaaS Meets AI in London. See you there.
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SaaStr 707: The Where, When, and How of AI with Theory Ventures, Open AI, MotherDuck and Lamini
SaaStr 707: The Where, When, and How of AI with Theory Ventures, Open AI, MotherDuck and Lamini
Hear the latest insights on AI from leading VC Tomasz Tunguz of Theory Ventures Theory Ventures, joined by Jordan Tigani, Founder and CEO of Mother Duck Maggie Hott, GTM at OpenAI, and Sharon Zhou, Co-Founder and CEO of Lamini. Together they discuss the new architecture for building Software as a Service (SaaS) applications with data & machine learning at their core, moderated by Tomasz.
The focus of the episode centers around the transformative role of data, which has become an integral part of the production stack. The speakers also delve into the implications of this shift and explore how leveraging data within the architecture empowers developers to create more robust, intelligent, and scalable SaaS solutions.
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SaaStr hosts the largest SaaS community events on the planet.
Join us in 2024 at:
SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20
SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200
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20Sales: How to Scale a Career While Scaling a Family, Strategies and Specific Tools To Help Maintain Work-Life Balance, What Companies Can Do To Empower Parents To Be Their Best Selves & How to Prevent Parental Leave Being an Inhibitor To Your Career
Today's 20Sales is a special Mother's Day edition where we are joined by 6 of the best sales leaders who also happen to be rockstar mothers.
The Profiles
Maggie Hott is on the GTM Team (Go-To-Market) at OpenAI. Before OpenAI, Maggie was Director of Sales @ Webflow and before Webflow spent an incredible 6 years at Slack.
Stevie Case is the CRO @ Vanta. Prior to Vanta, Stevie spent an immensely successful 6 years at Twilio as VP of Mid-Market Sales.
Renu Gupta is an advisor and sales consultant to some of the fastest-growing SaaS companies today. Previously she has held sales leadership roles at Slack, Thrive and Dropbox.
Lauren Schwartz is the VP Enterprise Sales @ Fivetran. Before Fivetran, Lauren spent 4 years at Segment as Senior Director of Enterprise Sales leading to their acquisition by Twilio.
Julie Maresca is the Head of Global Accounts at Atlassian. Prior to Atlassian, Julie spent an immensely successful 6 years at Slack in numerous roles including Head of Enterprise Sales for North America.
Jessica Arnold is the VP of Global Sales Development @ Amplitude. Before Amplitude, Jessica was the Senior Director for Inside Sales North America at Dropbox for close to 6 years.
In Today's 20Sales Mothers Day Episode We Discuss:
1.) How have you navigated growing in your career at the same time, growing your family?
2.) How do you balance your career and being a mother - when do you lean in and out?
3.) What are some specific strategies or tools that have helped you maintain a work-life balance?
4.) How do you prioritize your mental health and wellbeing while juggling your responsibilities at work and at home?
5.) How do you handle the guilt that many working mothers experience when they have to focus on their career?
6.) What are the unique challenges and advantages of being a mother in a sales leadership role?
7.) How has your experience as a mother influenced your leadership style and decision-making?
8.) How have you navigated going out on maternity leave without it having an impact on your career?
9.) America has one of the worst parental leaves of any country in the world. How can you advocate for parental leave if the existing policy isn't up to par?
10.) What are some ways that companies can create a more inclusive and supportive environment for working mothers in sales leadership roles?
20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process
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.
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?
