Sierra Logo

Sierra

Enterprise Sales Director - Strategic, Consumer Business Insights

Posted 6 Hours Ago
Be an Early Applicant
Remote
Hiring Remotely in Canada
Expert/Leader
Remote
Hiring Remotely in Canada
Expert/Leader
Lead Sierra’s largest and most complex enterprise sales opportunities across business units and geographies. Build trusted C-suite relationships, structure multi-million-dollar deals, manage risk and pricing, engage customers alongside founders, and shape strategic account and sales strategy. Use AI tools throughout the sales cycle for research, outreach, forecasting, summarization, and deal execution. The role requires executive-level communication, precision, and experience closing complex six- and seven-figure ACV deals.
The summary above was generated by AI
About us

At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.

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. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 

About the Consumer Business Insights team
  • Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.

  • This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.

  • Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.

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- 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
  • 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.

Even better...
  • 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.

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 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 

  • 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.

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 believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Similar Jobs

8 Hours Ago
Remote or Hybrid
Canada
Mid level
Mid level
HR Tech • Information Technology • Professional Services • Sales • Software
Own the full sales cycle for mid-market SaaS customers in Canada, from prospecting and relationship development through product demonstrations, forecasting, negotiation, and closing. Build pipeline through outbound activity, engage decision-makers, assess buying readiness, manage sales data in Salesforce, and network with consultants, partners, influencers, and industry events. Collaborate with Sales Engineers and Business Development representatives to drive new business.
Top Skills: HrisSaaSSalesforce
10 Hours Ago
Remote or Hybrid
Ontario, ON, CAN
Senior level
Senior level
Digital Media • Gaming • Information Technology • Software • Sports • Esports • Big Data Analytics
Develop and maintain relationships with VIP gaming customers, drive sales metrics and net revenue, promote loyalty, and deliver exceptional player experiences. The role executes responsible gaming policies, analyzes player data and trends, recommends customer solutions, and resolves escalations with internal teams. Candidates need a related bachelor's degree or five years of relevant gaming, hospitality, sales, or marketing experience, plus the ability to obtain and maintain required gaming licenses.
Top Skills: AI
10 Hours Ago
Remote
Canada
Senior level
Senior level
Cloud • Software
Own end-to-end B2B demand generation, including integrated campaigns, ABM, email nurture, organic social, website initiatives, conversion optimization, and performance reporting. Partner with Sales, Product Marketing, Customer Success, agencies, design, and product teams to generate measurable pipeline. The role requires strategic planning, hands-on execution, data-driven optimization, strong writing, and management of multiple concurrent programs, with emphasis on SaaS, technical audiences, open source, and product-led growth.
Top Skills: Claude CodeHubspotLinkedIn

What you need to know about the Vancouver Tech Scene

Raincouver, Vancity, The Big Smoke — Vancouver is known by many names, and in recent years, it has gained a reputation as a growing hub for both tech and sustainability. Renowned for its natural beauty, the city has become a magnet for professionals eager to create environmental solutions, and with an emphasis on clean technology, renewable energy and environmental innovation, it's attracted companies across various industries, all working toward a shared goal: advancing clean technology.

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account