Enterprise Sales Director

Sierra
San Francisco +1 more
Remote

Who this role is best for

Enterprise sales professionals with a track record in large account management and AI industry knowledge will find this remote-friendly role with a high-impact, cross-functional collaboration pattern

Best fit for

  • Individuals who can operate as AI-native sellers and leverage automation tools for efficiency
    — “Leverage AI tools across the full sales cycle to automate low-value tasks”
  • Professionals with strong verbal and written communication skills and a customer-centric mindset
    — “Strong communication skills: Exceptional verbal and written communication abilities”

Things to consider

  • The role may require in-person presence in major cities despite being remote-friendly
    — “We are primarily an in-person company based in San Francisco”
  • Candidates must be prepared to manage complex deal cycles with legal and finance stakeholders
    — “Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders”

How to stand out

  • Quantify your impact in managing large enterprise accounts and meeting revenue targets
    — “Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals”
  • Demonstrate your ability to build and maintain long-term relationships with key stakeholders
    — “Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers”
  • Showcase your analytical skills with examples of data-driven sales strategies or market trend analysis
    — “Ability to analyze market trends, identify opportunities, and make data-driven decisions”
Pace · Fast PacedCollaboration · HighAutonomy · MediumDecision Impact · CompanyLevel · Senior

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • identify and target potential customers
  • manage relationships with key decision-makers
  • close deals
Typical background
6-8 years of experience in enterprise sales

Skills & requirements

Required

Enterprise SalesComplex Deal CyclesNegotiationsSales StrategyCross-functional Collaboration

Preferred

AI Tools UsageAI Landscape Knowledge

Stack & domain

SalesNegotiationLead GenerationCustomer Relationship ManagementAI ToolsMarket AnalysisData-driven Decision MakingLeadershipCommunicationAnalyticalEnterprise SalesAICustomer Experience

About the role

Original posting from Sierra via Ashby

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 as 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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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. 

WHAT YOU'LL DO

  • Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
  • Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
  • Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
  • Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
  • Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
  • 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

  • 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
  • Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
  • Strong communication skills: Exceptional verbal and written communication abilities.
  • Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
  • Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.

EVEN BETTER...

  • Industry knowledge: 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 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.

Source: Sierra careers (Ashby)

Similar roles