Head of Sales
About The Position
As our Head of Sales, you will own the next stage of growth for our sales org while helping close the largest opportunities (player + coach role). We partner with mid-market and enterprise businesses as their AI-Enabled Risk Management Team. This requires developing a deep level of trust, showing a relentless amount of care for our prospective clients, handling their objectives, outlining thoughtful implementation plans etc. You’ll lead by example, developing best practices and then leveling up the entire team. You’ll set up systems to oversee the rest of the team, train them, and be consistently joining their most complex deals to help support. If you love high-stakes selling, enjoy building teams, and want a seat at the table shaping GTM, this role is for you.
Requirements
- 6+ years in B2B sales with a proven record of closing large, complex deals (mid-market or enterprise).
- A true player-coach: you’ve led teams and carried a number where you were still one of the top closers.
- Systems-minded: you’ll set up clear protocols across a fast growing team and constantly improve processes
- Strong executive presence with CFO/CEO-level buyers; credible, sharp, and consultative.
Responsibilities
- Personally lead and close our largest, most complex opportunities.
- Understand how we win by doing it yourself. Then productize the processes and playbooks so you can coach the team.
- Coach the team in live deals—not after the fact—through call participation, real-time feedback, and structured deal reviews.
- Build a culture of elite execution: high standards, crisp follow-through, and “how we win” discipline.
- Run weekly pipeline / forecast reviews focused on improving deal quality and closing behavior.
- Build a world class growth team – you’ll be responsible for recruiting, training, and execution. You’ll partner directly with the CEO.
- Set the standard for excellence in all our communications with prospective clients.
Benefits
- Competitive compensation that may include equity
- Flexible paid time off
- Comprehensive benefit plans for medical, dental, vision, life, and disability
- Flexible Spending Accounts (FSAs): Health Care FSA and Dependent Care FSA
- Commuter Savings Account
- Human Interest: 401(k) provider
- Time Off: Sick Leave, Family and Medical Leave, Flexible Time Off
- Paid Holidays: Observance of all major national holidays
- A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers
- Collaborative, transparent, and fun culture
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What This Job Offers
Job Type
Full-time
Career Level
Executive
Education Level
No Education Listed
