About this role
Sierra is building a customer-facing AI agent platform that partners with organizations managing everyday consumer and enterprise needs, spanning sectors like CPG, logistics, energy, and real estate. The Consumer Business Services team develops technology to make essential services faster, more reliable, and more human by handling tasks from order tracking to field service scheduling.
Leadership of the regional sales operations sits at the heart of this position, focusing on team mentorship, enterprise deal execution, and pipeline management. Successful candidates will bring a deep background in managing high-performing enterprise sales organizations and navigating complex transactions within established industries.
What you will do
- Hire, onboard, and develop account executives across the region while coaching reps on deal strategy, pipeline management, and execution.
- Own regional performance metrics, maintain forecast accuracy, and inspect pipeline quality to unblock stalled enterprise deals.
- Drive consistent execution of the sales process in partnership with revenue operations to ensure clean data and clear insights.
- Participate directly in key customer and prospect conversations to help representatives navigate complex buying committees and late-stage deals.
- Support pricing, negotiation, and close strategy for major accounts.
What you need
- Possess at least 15 years of selling experience in enterprise customer-facing sales roles, identifying and closing large accounts.
- Bring 10 or more years of people leadership experience managing, mentoring, and developing high-performing enterprise sales teams.
- Demonstrate a track record of running and managing end-to-end complex deals valued at $1 million or more.
- Exhibit exceptional verbal and written communication abilities for high-stakes negotiations and internal alignment.
- Apply an analytical mindset to evaluate market trends, identify opportunities, and make data-driven decisions.
Nice to have
- Familiarity with the AI landscape, key players, emerging trends, and fluency with AI tooling and workflows
- Experience building go-to-market strategies, sales teams, and sales motions from scratch or early-stage growth
Benefits
- Flexible unlimited paid time off
- Medical, dental, and vision benefits for employees and families
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave and fertility and family building benefits through Carrot
- On-site lunch, snacks, coffee, discretionary benefit stipend, and free alphorn lessons
Questions candidates ask
What is the remote work policy for this position?
Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
What compensation is associated with this role?
The salary ranges from $500K to $520K, with offers of equity and commission available.
What kind of teams will this leader work with?
The Consumer Business Services team partners with businesses spanning consumer products, commercial real estate, logistics, energy, utilities, and professional services.