Enterprise Sales Director - Majors

WHAT YOU'LL DO

- Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.

- Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.

- Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.

- Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.

- Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.

- Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.

- Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

WHAT YOU'LL BRING

- 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.

- Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

- Proven ability to multi-thread and build trusted relationships across customer C-suites.

- Exceptional verbal and written communication.

- Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.

EVEN BETTER...

- Familiarity with the AI landscape, key players, and emerging trends.