Sierra
Enterprise Sales Director - Strategic, Retail
$360K–$380K
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; the posting also specifies experience managing a $1M+ quota.
About the job
Leads Sierra’s largest strategic retail sales opportunities, building executive customer relationships and structuring complex deals for its AI agent platform.
What you'll do
- Lead complex, multi-business-unit and multi-geography deals, including deal design and risk management.
- Build trusted relationships with customer executives and working teams, and engage Sierra co-founders in customer conversations.
- Shape strategy for key accounts and use AI tools throughout the sales cycle.
What they ask for
- 10–12+ years of enterprise or strategic sales experience owning large, complex accounts.
- Record of closing multi-million-dollar, multi-stakeholder deals across business units and geographies.
- Experience managing a $1M+ quota and end-to-end 6- and 7-figure ACV deals.
- Deep C-suite relationships; expertise in deal structuring, risk navigation, and pricing; exceptional executive communication.
Nice to have
- Deep familiarity with the AI landscape and ability to speak to technical and business stakeholders.
- Experience working alongside founders or executives with strategic customers.
Pay
$360K – $380K (base salary); commission amount not stated
AI focus
Sell Sierra’s customer-facing AI agent platform to retail brands and use AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.
Model-written summary · the original posting is authoritative