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.
Our values- Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
- Customer Obsession: We deeply understand our customers' business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
- Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn't right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
- Intensity: We know we don't have the luxury of patience. We play to win. We care about our product being the best, and when it isn't, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
- Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other's personal and professional achievements.
What we offerWe want our benefits to reflect our values and offer the following to full-time employees:
- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for you and your family
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family building benefits through Carrot
- Lunch, as well as delicious snacks and coffee to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
