Lessons from Maggie Hott

As a prominent figure in the tech industry and a key leader in OpenAI's go-to-market strategy, Maggie Hott has shared numerous insights on building and scaling successful sales organizations. Drawing from her extensive experience at companies like Eventbrite, Slack, Webflow, and OpenAI, her advice offers a valuable playbook for founders and sales leaders.

On Hiring and Building a Team

Prioritize exceptional talent. "One exceptional hire is better than three average hires." [1] This principle is crucial even if it means slowing down the hiring process, as A-players attract other top talents. [2]
Avoid the "logo trap." Don't assume that a candidate from a big-name company is automatically a good fit for a startup. It's essential to understand what they have built from scratch versus what they have operated within an existing framework. [2]
Hire builders, not just operators. Early-stage companies need individuals who can create and scale processes, not just manage existing ones. [2]
Look for mission-aligned candidates. Hire people who are motivated by the company's mission and objectives, not just the allure of the vision. [1]
Build teams, not just a collection of talented individuals. A team of top performers who cannot collaborate will lead to bottlenecks. Focus on creating a team with complementary skills that fit together like a puzzle. [1]
Don't compromise on the hiring bar, especially during hypergrowth. It's tempting to lower standards to fill seats quickly, but this can be detrimental in the long run. [1]
A mis-hire is incredibly costly. A single bad hire can cost over a million dollars when factoring in recruitment time, training, lost deals, and cultural disruption. [1][2]
The founder is the head of sales until a repeatable motion is established. Founders must own the sales process until it's proven that a non-founder can successfully sell the product. [1]
Avoid hiring a senior sales leader too early. Bringing in a CRO when you only have a couple of account executives is a mistake. A repeatable sales motion and clear playbooks must be in place first. [1]
Your first sales hires should be versatile generalists. In the early days, you need people who can jump in and handle various tasks. [1]
Avoid "lone wolves" in early hires. Prioritize collaborative individuals over those who prefer to work in isolation. [1]
Trust your gut in the hiring process. If something feels off during an interview, it probably is. [1]
Act quickly on hiring mistakes. The most compassionate action for the company and the individual is to address a bad hire swiftly. [1]
Leverage your network for hiring. Don't hesitate to use your investors, advisors, and other connections to find and vet candidates. [1]
In interviews, distinguish between tactical skills and behavioral traits. Ask about what a candidate has built and how they've mentored others (tactical), as well as how they handle failure and collaborate (behavioral). [1]
A key red flag in an interview is blaming others for failures. Look for candidates who take ownership of their mistakes and demonstrate a growth mindset. [1]

On Go-to-Market Strategy and Sales

Old playbooks don't always apply in AI. Be prepared to design organizations and strategies around the product and not legacy structures. [1]
For new AI products, consider a dedicated "tiger team." Instead of training everyone to sell a new product, a small, focused team can move faster and be more willing to make mistakes. [1]
Product-led growth (PLG) and sales are not mutually exclusive. PLG is excellent for driving initial adoption, but a sales team is critical for moving upmarket and securing strategic deals. Plan for both from the beginning. [1][2]
Founders with a technical background often overlook the sales upgrade path. It's crucial to think about how the product will evolve to support a sales motion early on. [1]
Define your Ideal Customer Profile (ICP) early. Look at your current successful customers to identify common traits and pain points to find similar prospects. [3]
Take a "crawl, walk, run" approach to your ICP. Start with a narrow and focused list of no more than 100 companies. [3]
Enterprise sales have long and complex cycles. Be prepared for 9 to 12-month sales cycles with multiple stakeholders and procurement processes. [3]
Enterprises expect high levels of support and uptime. Startups may not be able to meet the demands for 99.999% uptime and immediate support. [3]
Avoid deep customization for early enterprise customers. This can distract from your product roadmap. [3]
Use the 10-80-10 rule for cold emails. Personalize the first and last 10% of the email to make it feel specific to the recipient, while the middle 80% can be scalable content. [4]
Pilots should be reserved for your most qualified customers. Don't offer a pilot to everyone who asks. It's crucial to understand the "why" behind the request and have clear success metrics. [5]

On Leadership and Culture

Founders need to learn to "give away their Legos." To scale, leaders must delegate responsibilities to seasoned experts and trust them to do their jobs without micromanagement. [1]
The first "Lego" to give away should be the one that drains you the most. This allows you to focus on other critical areas of the business. [1]
Build a culture of accountability. This starts with ensuring every employee understands how their role contributes to the company's mission. [3]
Make revenue everyone's business. Talk about revenue and key metrics like ARR and NRR in company-wide meetings to align everyone. [3]
Create "customer wins" and "customer losses" channels. These Slack or communication channels keep the entire company connected to the customer experience and provide valuable feedback. [1][3]
Customer obsession is everyone's job. At Slack, non-sales leaders were assigned as directly responsible individuals for top customers, which accelerated the integration of customer feedback into the product roadmap. [1]
Invest in leadership development. Provide executive coaching and emotional intelligence training to equip managers to handle not just people, but also conflict and culture. [1]
Your managers are your cultural backbone. They are responsible for more than just managing people. [1]
A culture of accountability can pull a company through a crisis. Recalling a major hack at Slack, Hott emphasized that the team's deep care for the product, customers, and each other was what enabled them to recover. [3]

On Product-Led Growth (PLG) and Enterprise Sales

There are four key signs you're ready to layer on a sales team. You understand the pain point your product solves, you're generating around $1-2 million in ARR, you have product-market fit, and you can sell to customers outside your immediate network. [6]
Differentiate your enterprise product offering. Don't just charge more for the same product. Add features like advanced security, SSO, and dedicated customer support to justify the higher price point. [6]
Invest in customer success before sales. Acquiring a new customer costs five times more than retaining one. Successful customers provide early feedback, word-of-mouth marketing, and valuable case studies. [3]
Founders should handle the first 15 deals themselves. This founder-led sales approach is crucial for understanding the customer and the sales process. [3]
Hire a customer success manager after your first five customers. This ensures personalized support and helps you do things that aren't scalable in the early days to ensure customer success. [3]

On Personal Growth and Advocacy

Life throws unexpected challenges, much like building a startup. Hott openly shares her experience as a cancer survivor, drawing parallels between personal resilience and the perseverance required in entrepreneurship. [3][5]
One of her "superpowers" is the ability to see around the corners of hypergrowth. This foresight helps her avoid common mistakes when scaling go-to-market teams. [3]
Advocate for better parental leave policies. Hott provides a four-step framework for employees to advocate for change: educate the company, gather data from comparable companies, find an executive sponsor, and be clear in your asks. [7]
Be specific about your needs when planning parental leave. Create a detailed coverage plan that outlines when you want to be contacted and for what reasons. [7]
Don't be ashamed to advocate for yourself. This includes asking for a ramped quota upon returning to work and protection for your accounts while you're out. [7]
Being a role model for her daughters is a primary motivation. She emphasizes the importance of having a fulfilling career while being present for important family moments. [8]
Technology can be a key enabler of work-life balance. Tools like Gong have allowed her to stay close to her team's deals while managing a demanding schedule. [8]
Remote and hybrid work environments can accelerate success. The flexibility allows for greater integration of work and personal life. [8]
Partner deeply with your customers to create value. Hott shares the story of OpenAI's work with Moderna to create DoseGPT, emphasizing that the goal is to save lives, not just time. This deep partnership is what creates "everlasting customers." [3]

Learn more:

Lessons from Maggie Hott

On Hiring and Building a Team

On Go-to-Market Strategy and Sales

On Leadership and Culture

On Product-Led Growth (PLG) and Enterprise Sales

On Personal Growth and Advocacy

Written by Antoine Buteau

Lessons from Pat Grady, partner at Sequoia

Lessons from Saumil Mehta