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Sales Programs, Sales Enablement

Sierra

San Francisco, CAFull-time$170–220K/yrPosted todayStill listed today

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At a glance

Compensation
$170–220K/yr
Location
San Francisco, CA
Schedule
Full-time
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Job overview

Sierra is hiring for a sales programs and enablement role focused on owning sales plays from intake through retirement. The role partners with Product Marketing, Product, Sales Leadership, and Sales Engineering to prioritize and build play assets, train sellers and SEs, measure results, and adapt plays for regional teams. The candidate should bring at least four years of relevant experience at a B2B software company.

Skills & qualifications

RequiredNice to have

Skills

Sales EnablementSales ProgramsProduct MarketingSales Play DevelopmentGo-to-Market ProgramsPrioritizationWritingFacilitationData AnalysisAI SalesEnterprise Software SalesHighspotSeismicGongSellingSales Engineering

Qualifications

4+ Years Relevant ExperienceB2B Software Company Experience

Benefits

Paid Time Off
Medical Insurance
Dental Insurance
Vision Insurance
401(k) Match
Parental Leave

Full job description

About us Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. 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 a commitment to balancing Family along the way. 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. What you’ll do

  • Own the end-to-end lifecycle of sales plays: intake, design, build, launch, adoption, and retirement

  • Work with Product Marketing, Product, Sales Leadership, and Sales Engineering to decide which plays get built and in what order

  • Build play assets: messaging, discovery guides, demo flows, competitive battlecards, objection handling, and customer proof points

  • Train sellers and SEs on new plays through live sessions, async content, and practice

  • Define how each play's success is measured (usage, pipeline influence, win rate where attributable) and report on it

  • Retire or update plays that aren't working

  • Create the intake and prioritization process for play requests

  • Build plays so they can be adapted for regional teams, including our London office

What you’ll bring

  • 4+ years in sales enablement, sales programs, product marketing, or a related field at a B2B software company

  • Experience building and launching sales plays or go-to-market programs for both sellers and technical teams

  • Ability to say no and prioritize across competing requests from senior stakeholders

  • Strong writing and facilitation skills

  • Comfort with data, and honesty about what can and can't be attributed to enablement

Even better…

  • Experience in AI or enterprise software sales environments

  • Experience with enablement and conversation-intelligence tools (e.g., [Highspot, Seismic, Gong])

  • Prior experience as a seller or SE

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.

How this job compares

Set against the 1,038 open Sales Enablement jobs on Olive Jobs, counted November 5, 2026.

Pay
  • This posting$170–220K/yr
  • California median$147–217K/yr117 salary ranges
  • US median$123–191K/yr820 salary ranges

This range's midpoint, $195K, is 8% above the California median midpoint ($180K) — in the middle half of Sales Enablement salary ranges in California.

Openings
Olive Jobs lists 145 open Sales Enablement jobs in California and 1,038 across the US. 12% of them nationwide are listed as remote or flexible.
Hiring the most in California
Experience
This posting asks for at least 4 years of experience — less than three in four Sales Enablement postings that state a minimum ask for (median 7 years, across 829 postings).
Education
237 of the 1,038 open Sales Enablement jobs (23%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on November 5, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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