Sierra
Enterprise Sales Director - Strategic
$300K–$345K
US - Remote +3 · Remote · Director · Full-time · Posted Aug 5, 2026
- Location
- US - Remote
San Francisco, CA
New York, NY
Atlanta, GA - Experience
- 10–12+ years of enterprise/strategic sales experience.
About the job
Leads Sierra’s largest strategic enterprise sales opportunities, structuring complex deals and building executive customer relationships.
What you'll do
- Lead large multi-business-unit and multi-geography opportunities, including deal structuring, pricing, and risk management.
- Develop trusted relationships with customer executives and teams; engage Sierra co-founders in customer pitches.
- Shape strategic account and sales-team approaches while using AI tools throughout the sales cycle.
What they ask for
- 10–12+ years of enterprise or strategic sales experience owning large, complex accounts.
- Track record closing multi-million-dollar deals involving multiple stakeholders, business units, and geographies.
- Experience managing a $1M+ quota and executing complex 6- and 7-figure ACV deals.
- Strong C-suite relationships, complex deal-structuring and pricing expertise, and exceptional executive communication.
Nice to have
- Deep familiarity with the AI landscape and ability to address technical and business stakeholders.
- Experience working alongside founders or executives with strategic customers.
Pay
$300K – $345K (base salary)
AI focus
Use AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution; continuously experiment with new tools to automate low-value tasks and improve sales productivity.
Model-written summary · the original posting is authoritative