Proven success hiring and developing top-performing enterprise sellers
Experience scaling sales at a pre-Series C startup
Responsibilities
Build and lead a high-performing enterprise sales team
Own frontline management: set quotas and manage pipeline
Lead by example, prospect, build champions, and close deals
Develop and execute outbound strategy in collaboration with leadership
Experiment with outbound techniques and scale successful methods
Identify and implement tools and processes for growth acceleration
Help shape Oso's sales culture and inspire the team
Benefits
Competitive health, dental, and vision coverage
Mental healthcare for employees and their families
Unlimited access to financial advisors
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
Full Job Description
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.
