Head of Sales
jawnt
About Jawnt
We work with universities, healthcare systems, governments, and enterprise organizations to offer a valuable benefit that saves employees time, reduces costs, and supports sustainable choices. We’re trusted by critical enterprises to get their employees to work reliably, sustainably, and affordably.
About The Role
You will build and lead the sales organization. You will refine and execute our go-to-market strategy, build pipeline, manage and hire a team, and personally close key deals. You will report to CEO and work closely with Marketing, Product, and Customer Success.
You’ll learn from Jawnt’s early wins and shape a comprehensive strategy, team, and culture. This is a foundational role, building the team that will enable Jawnt to capture the $20 billion commuter benefits market, displace legacy incumbents, and drive forward technology that is the backbone of our cities.
About You
You are...
A player/coach who’s both strategic AND hands on:
- You thrive when carrying a quota, managing a team, and planning the big picture
- You know what it’s like at a VC-backed growth stage company going through an inflection point and have a proven track record scaling B2B Enterprise SaaS companies from an early stage
Execution-focused:
- Own and/or coach reps on strategic, big ticket, complex deals, taking on processes themselves when need be
- Establish a scalable sales process with clear metrics and forecasting capabilities
A storyteller:
- Understand customer needs and wants, and can translate them into demand creation
Team-centric:
- Responsible for recruiting, onboarding, and managing a high-performing sales team
A leader:
- Demonstrate excellence daily internally to CEO, team, and investors, and externally to our customers and partners
- Strong communication and relationship-building skills
Nice to haves:
- Experience selling HR/benefits solutions or other workplace platforms
- Based in San Francisco, Philadelphia, New York, or Boston in that order; must be willing to travel regardless
Typical Responsibilities
- Develop and execute sales and marketing strategies to achieve revenue targets
- Build, lead, and scale a high-performing sales organization
- Create and optimize the sales process, from lead generation to closing
- Represent Jawnt at industry events and with key stakeholders
- Build partnerships / other channels as appropriate for customer acquisition
- Work with product team to ensure product roadmap aligns with market needs
- Analyze market trends and competitor activities to inform strategy
- Manage and optimize budget
- Collaborate with customer success to ensure strong retention and expansion
Compensation
- Competitive salary + performance bonus / commission → $200-225k base; $350-400K OTE (target of 60/40 base/commission split)
- Equity package → 0.75 - 1.0%
- Comprehensive commuter benefits (of course)
- Other benefits (health, remote/hybrid, flexible work, 401k, etc).
Process
1. Phone screen (30 mins with Cofounder)
2. Interview Loop (60 mins):
Three 20-minute meetings with Advisor, Cofounder, and Investor
3. Deep dive + first year plan (90 mins)
- Deep dive into prior Sales org structure
- Review proposed first year plan
4.1. Meet the team (60 mins)
Opportunity to chat with other team members
4.2. Reference checks