Head of Sales

What you'll do

• Build and lead a high-performing enterprise sales team, including hiring, onboarding, coaching, and career development.
• Own frontline management: set quotas, manage pipeline, review deals, and drive consistent overachievement.
• Lead by example — prospect, run discovery, build champions, run POCs, negotiate, and close enterprise deals.
• Develop and execute our outbound strategy, refining pitch and positioning in collaboration with leadership, product, and marketing.
• Experiment with outbound techniques (calling, email, social) and scale what works.
• Identify and implement tools, processes, and playbooks to accelerate growth.
• Help shape Oso’s sales culture, setting ambitious goals and inspiring the team to deliver.

Who you are

Hands-on leader. You inspire by doing: closing deals, refining messaging, and coaching reps daily.

Talent builder. You know how to hire, develop, and retain exceptional enterprise sellers.

Strategic executor. You can both design the playbook and run it yourself.

Owner. You measure yourself on outcomes, not activity, and think like a company-builder.

Resilient. You embrace challenges and thrive in the ambiguity of startup growth.

Growth-minded. You self-reflect, seek feedback, and help others grow with you.

Customer-obsessed. You want to understand our users’ world and solve their problems above all else.

Requirements

• 7+ years of enterprise B2B SaaS sales experience.
• 3+ years in frontline management.
• Consistent track record of exceeding quota.
• Proven success hiring, developing, and leading top-performing enterprise sellers.
• Experience scaling sales at a pre-Series C startup

Benefits

In addition to cash compensation, Oso offers a Total Rewards package that includes equity grants, health benefits, and more:

• Competitive health, dental, and vision coverage
• Mental healthcare to all employees and anyone in their family through Spring Health
• Unlimited access to financial advisors through Northstar
• Equity Package
• Unlimited paid time off (PTO)
• Paid parental leave
• Flexible work options
• One Medical Membership
• Quarterly hackathons... and prizes!
• Free team lunches every month

The OTE range for this role is between $325,000-$350,000/year plus equity and accelerators. Your exact offer will vary based on a number of factors including experience level, skillset, market location, and balancing internal equity relative to peers at the company.