Head of Sales

Sola Insurance

$150K — $180K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years in sales leadership or management roles
  • Demonstrated ability to coach and develop talent
  • Experience in building training and onboarding programs
  • Proven track record in managing sales forecasts and performance
  • Strong understanding of sales methodologies like MEDDIC or Sandler

Responsibilities

  • Lead the sales and account management team and facilitate growth
  • Train and coach team members on agency engagement and sales techniques
  • Recruit and onboard new sales staff prioritizing strong hires
  • Own the sales forecast and ensure trusted metrics are in place
  • Create and optimize CRM workflows and sales automation systems
  • Collaborate with marketing to identify target agencies and improve outreach strategies

Benefits

  • Equity stake in the company
  • Comprehensive medical, dental, and vision coverage for family
  • Daily catered lunches for staff
  • Retirement plan (401(k))
  • Paid parking incentives
  • Membership to One Medical for health services
Full Job Description
About the Role
You'll lead our sales and account management team, currently seven people, with plans to grow to around 20 over the next year. The structure that got us here needs to evolve. You'll work directly with our CEO and Head of Finance to rebuild how we hire, train, manage, and forecast for the next stage of growth.

Your job is to help us become a trusted, indispensable partner to each agency, deepening those relationships over time and earning a larger role in their business. You'll make Sola a place where great salespeople come to learn and build their careers. That means coaching the team, hiring well, developing future managers, and building systems that make us better as we grow.

You're joining while we're still small enough for your decisions to shape the entire sales organization. You'll have the opportunity to build it, lead it at increasing scale, and grow your own career alongside the company.

We'll trust you to make decisions using your experience and the data. You'll have the authority to act, responsibility for the results, and equity in the business you help build.
What You'll Do
  • Develop the team. Build onboarding and ongoing training. Run weekly 1:1s, call reviews, and role-play. Teach reps to understand an agency's needs, qualify fit early, and agree on clear commitments. Address underperformance directly and develop future managers.
  • Grow agency relationships. Help agencies move from onboarding to their first policy and become consistent producers. Understand their goals, help them succeed, and earn a larger share of their business. Build clear ownership across sales and account management.
  • Recruit and grow the team. Make recruiting a priority. Hire strong sellers and account managers, and plan territories, compensation, ramp, and career progression with leadership.
  • Own the forecast. Understand agency productivity, conversion, retention, and rep capacity. Use methodologies like MEDDIC, MEDPICC, Sandler, or Challenger to qualify opportunities so the forecast that rolls up from them is one you can trust. Work with Finance to set targets, explain misses, and act early.
  • Build the systems. Own CRM workflows, dashboards, and automation. Implement tools that improve prospecting, coaching, and follow-through.
  • Build outbound and expand our channels. Work with Marketing to define who we pursue, test outreach, and turn successful approaches into a repeatable source of productive agencies.

Insurance experience isn't required.

Benefits
  • Early stage equity
  • 100% paid medical, dental, and vision coverage for you, your spouse, and your children
  • Daily catered lunch
  • 401(k)
  • Paid parking
  • One Medical membership

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