At a Glance
- Tasks: Lead complex enterprise sales deals and build trusted relationships with C-suite executives.
- Company: Join Sierra, a cutting-edge AI platform focused on enhancing customer experiences.
- Benefits: Enjoy flexible paid time off, comprehensive health benefits, and a supportive work culture.
- Other info: Diverse and inclusive environment that values unique skills and experiences.
- Why this job: Make a real impact in the AI landscape while working alongside industry leaders.
- Qualifications: 10+ years in enterprise sales with a proven track record of closing multi-million-dollar deals.
The predicted salary is between 135000 - 165000 $ per year.
About us: At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family.
What you'll do:
- Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
- Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
- Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
- Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
- Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
- Operate as an AI-native seller: Leverage AI tools across the full sales cycle to automate low-value tasks and reinvest that time into high-value customer relationships.
What you'll bring:
- 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
- Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
- Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
- Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
- Mastery of complex deal structuring, risk navigation, and pricing.
- Exceptional executive communication and a reputation for precision and trust.
- Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.
- Experience operating alongside founders/executives in front of strategic customers.
- Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Our values:
- Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness.
- Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes.
- Craftsmanship: We get the details right, from the words on the page to the system architecture.
- Intensity: We know we don’t have the luxury of patience. We play to win.
- Family: We know that balance and intensity are compatible, and we model it in our actions and processes.
What we offer: We 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.
Be you, with us: We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We encourage you to apply even if your experience doesn't precisely match the job description.
Enterprise Sales Director in Toronto employer: Sierra
Sierra is an exceptional employer that fosters a vibrant work culture rooted in trust, customer obsession, and craftsmanship. Located in the heart of San Francisco, we offer flexible paid time off, comprehensive health benefits, and unique perks like free alphorn lessons, all while supporting employee growth through collaboration and innovation in the rapidly evolving AI landscape. Join us to be part of a team that values balance and intensity, ensuring that your professional journey is both rewarding and fulfilling.
