Startup Sales (Fireside Chat)
This content is intended for past participants of First Row’s workshops and is on an invite-only basis. If you’d like to share this content, please reach out to Yoko or Minda.
About
We welcomed two fantastic enterprise sales leaders for a conversation about the ins and outs of building a founder-led sales process and how to hire professional sales leaders without the common pitfalls.
Presentation
Our Guests
Kirsten Schaub // Transitioning from founder-led sales to professional sales. Kirsten’s depth of experience comes from her 12 years at DocuSign building the sales organization around the life sciences vertical. She works with founders and founding teams on both the tactical and strategic paths of setting up and scaling Sales/GTM motions for B2B sales. Her focus is areas where the founder/exec team needs to use a strategic lens around their GTM motion but it’s not stage-appropriate to bring in sales leadership. Key focus areas are pricing/packaging strategy, sales pipeline organization, deal strategy, and basic product marketing to tell the story to prospects. A particular area of interest is helping founders set up their Founder Led Sales Motion and continuing to tune that motion through growth phases up to and including those first key Sales/Business Development/Customer Success hires. // kirstenschaubconsulting@gmail.com
Matt Rubright // Founder-led sales. Matt has done enterprise sales in multiple contexts at roles in early-stage startups (Candidate, Datagrail), Silicon Valley Bank, and more. Matt impresses us with his knack for taking big functional areas, building playbooks and seeing the big picture. He now works with companies to build their GTM processes and playbooks.
(Facilitator: Minda Brusse, First Row Partners)
Topics Covered
Founders as unexpected sellers. Most founders didn't start a startup to "get into sales," but founders and CEOs are always selling employees, customers, investors, and the press. Founders frequently feel “incompetent” as professional sales and want to hire an expert at the earliest point possible. Especially because of revenue pressure. Why doesn't this work as well as hiring for other functions?
“Mistakes Were Made” Launching and scaling enterprise sales is often a bumpy road and mistakes are common. Some have bigger consequences than others.
Hiring right + scaling up How is hiring for this function inherently different from other functions like engineering, HR, and marketing? What is the optimal path for this transition?
Key Takeaways
What tips do you have for cold calling? Don’t just “let it happen.” Figure out structure & basic process - whether it’s email/LinkedIn/follow-up/etc. Then set some targets and be accountable to yourself. Filter, and be tight about who you’re reaching out to - list is more like 50-100, not 2,500.
Use who you are as a founder to your advantage. “Where is your expertise (as a founder)?” How can you leverage that?
Most of what you’re doing for the first time should be unscalable. Instead of being persuasive that they (potential customer) could do this work, figure out how far you can take the work to get the customer as close as possible to that moment of delight with minimal effort on their end. THEN you have a better sense of where you’ll build in the automation.
Learning YOUR Sale. Figure out where your buyers are, what newsletters do they read, what communities are they in? How can you put yourself into those shoes? Using jargon / words that you’re hearing from your audience. “The amount of credibility you gain by talking like your customers is big.”
How do you get started building a sales process? Start simple - with Google Doc that you’re constantly refining. Who am I selling to? What is my sales process? What words do they use to describe things?Constantly updating and adding notes - those revisions can help you as you think about handing things off or building a structured process. This basic hygiene in documenting who you’re talking to is an early movement towards a CRM.
Before you hire (someone for sales) you need enough of a pitch/playbook to understand what the customer wins look like.
Often seeing that founders aren’t asking “for the sale”. What you should be focused on is making the first customers profoundly successful and raving fans.
Additional Food For Thought
Whale (big enterprise customer) hunting and the signals that you might get (and should ignore) from enterprise. They can also detour you on features to build and put a deal through endless approval cycles.
Variable comp - a good sales person will wants variable comp (i.e. their comp reflects if they bring in a very large deal). Be ready for the cash flow implications.