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?

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?

Leading VC Tomasz Tunguz of Theory Ventures, Jordan Tigani of MotherDuck, Maggie Hott of OpenAI, and Sharon Zhou of Lamini discuss the transformative role of data in building SaaS applications. They explore the impact of AI on application development, democratizing technology with LLMs, using licensed and synthetic images, AI's impact on investment firms and job roles, and the future of AI, education, and scalable domain experts.