Enterprise Sales Director

About the role

You will independently drive complex enterprise deals end-to-end, managing a broad enterprise book with strong autonomy as you lead 6- and 7-figure deal cycles from prospecting through to close. You will multi-thread to the C-suite, leading VP-level conversations and building durable relationships across customer organizations to earn credibility quickly with new stakeholders. You will manage risk proactively by identifying and managing deal risk early and building rigorous stakeholder maps for every account. You will make the hard calls, partnering with your manager and, at the senior level, operating more independently on pricing, escalation timing, exec alignment, and deal strategy, coming to the table with a clear point of view rather than only surfacing problems. You will bring in Sierra's co-founders effectively for executive engagement when it moves a deal, raising the bar as a visible, steady leader who proactively elevates the team's standard without being asked. You will operate as an AI-native seller, leveraging AI tools across the full sales cycle for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

Key facts

What you'll do

• Independently drive complex enterprise deals end-to-end, managing a broad enterprise book with strong autonomy to lead 6- and 7-figure deal cycles from prospecting to close.
• Multi-thread to the C-suite, leading VP-level conversations, building durable C-suite relationships across customer orgs, and earning credibility quickly with new stakeholders.
• Manage risk proactively by identifying and managing deal risk early and building rigorous stakeholder maps for every account.
• Make the hard calls, partnering with your manager and, at the senior level, operating more independently on pricing, escalation timing, exec alignment, and deal strategy, coming to the table with a point of view rather than only surfacing problems.
• Leverage leadership and co-founders by bringing in Sierra's co-founders effectively for executive engagement when it moves a deal.
• Raise the bar as a visible, steady leader on deal teams, proactively elevating the team's standard without being asked.
• Operate as an AI-native seller, leveraging AI tools across the full sales cycle for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
• Analyze market trends, spot opportunities, and make data-driven decisions to refine strategy and execution in complex enterprise environments.
• Partner cross-functionally with product, implementation, and customer success to ensure seamless deal execution and long-term customer outcomes.
• Own the full sales cycle including discovery, solutioning, negotiation, contracting, and post-sale expansion within assigned enterprise accounts.
• Develop and maintain a clear, actionable pipeline forecast and revenue plan in collaboration with leadership and RevOps.
• Serve as an expert on Sierra's platform and AI capabilities, articulating differentiated value to enterprise buyers in highly competitive situations.

Requirements

• 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 analyzing market trends, spotting opportunities, and making data-driven decisions.
• Demonstrated success operating in fast-paced, ambiguous environments with high ownership.
• Track record of exceeding quota and delivering predictable, repeatable results in an enterprise sales role.
• Strong judgment and maturity to operate with executive presence and discretion in sensitive negotiations.

Nice to have

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

Practical notes

This role is full_time and remote within the United States.

Eligibility and hard bars from SOURCE

• You must have 8-10 years of enterprise customer-facing sales experience identifying and closing large accounts.
• You must have experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• You must demonstrate proven ability to multi-thread and build trusted relationships across customer C-suites.
• You must possess exceptional verbal and written communication skills.
• You must have an analytical mindset, analyzing market trends, spotting opportunities, and making data-driven decisions.
• You must operate effectively in fast-paced, ambiguous environments with high ownership.
• You must have a track record of exceeding quota and delivering predictable, repeatable results in an enterprise sales role.
• You must show strong judgment and maturity to operate with executive presence and discretion in sensitive negotiations.