Head of Sales
At a glance
Leadership Sales Leadership role at Oso. New York · full-time · $325,000–$350,000 OTE.
Growth Roles summary, based on the employer's posting.
What you'll do
- Build the enterprise sales team through hiring, onboarding, coaching, and career development
- Set quotas, inspect pipeline, review deals, and push the team toward consistent quota overachievement
- Personally prospect, lead discovery, develop champions, run POCs, negotiate, and close enterprise opportunities
- Create the outbound motion with leadership, product, and marketing, then scale effective calling, email, and social tactics
- Introduce sales tools, operating processes, and playbooks while shaping the team’s sales culture
What you bring
- At least seven years selling enterprise B2B SaaS solutions
- At least three years managing frontline sales teams
- A sustained record of beating quota and winning enterprise business
- Evidence that you have hired, developed, and led high-performing enterprise sellers
- Experience expanding sales within a startup before Series C
Who this fits
You’ll suit a hands-on sales builder who can design the playbook, sell directly, and coach reps day to day. The role is based in New York with a hybrid setup and works directly with the Founder/CEO and Fractional CRO. It is a founding sales leadership position with responsibility for building and leading the team.
From the employer
Old problem, new $25B+ market
Companies like AWS, Stripe, and Twilio have shown that if a technology isn't core to your value proposition, you should offload it. Still, every engineering team builds and rebuilds one piece: authorization, how you control who has access to what in your app. We intend to change that.
We see a world where developers never roll their own authorization again, and instead say, "Just use Oso" – the same way you might say, "Oh, you should just use Postgres for that." In doing so, we're creating the $25B+ authorization market.
Why Oso?
We have the lead – in traction, capital, and team.
Traction: Oso is used by thousands of companies from startups to the Fortune 500, like Wayfair, ProductBoard, Vanta, Brex, Verizon, ZoomInfo, and Duolingo.
Capital: We're backed by the world’s best investors, including Sequoia, Felicis, and a standout group of infrastructure founders and operators: Olivier Pomel (Founder, Datadog), Dev Ittycheria (CEO, MongoDB), Armon Dadgar (Founder, HashiCorp), Edith Harbaugh (Founder, LaunchDarkly), Guy Podjarny (Founder, Snyk), Paul Copplestone (Founder, Supabase), Christina Cacioppo (Founder, Vanta), and Calvin French-Owen (Founder, Segment).
Team: We've spent 5+ years going deep on the domain. We've met with thousands of engineering teams and know more about this problem than anyone. And we have two of the best developer go-to-market leaders on earth who have done it before at MongoDB and Snyk.
Why now?
We're at an inflection point. What it takes to get from where we are today to a world where developers say “Just use Oso” is going to be different. And we see that.
The opportunity is for you to join at this inflection point, in a role that’s bigger and different than usual.
What you'll do
You’ll be the founding sales leader at Oso and define how we go to market. You’ll work directly with our Founder/CEO and Fractional CRO to:
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.
Oso is an equal opportunity employer. All applicants will be considered for employment regardless of race, color, national origin, religion, sex, age, disability, sexual orientation, gender identity, veteran or disability status.
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