---
title: 'Global Head of Sales Enablement at Sierra'
canonical: 'https://feeny.ai/job/global-head-of-sales-enablement-sierra-san-francisco-p9exergmk0zn'
type: 'job'
last_seen: '2026-09-12'
---

# Global Head of Sales Enablement at Sierra

- **Company:** [Sierra](https://feeny.ai/companies/sierra)
- **Location:** San Francisco, CA
- **Compensation:** $215k–$265k
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-06-12
- **Last confirmed live:** 2026-09-12
- **Apply:** https://jobs.ashbyhq.com/Sierra/8807d554-7c2c-4843-a74b-9f4eafe986ff/application

**Skills:** AI-powered enablement tools, Content platforms

> Sierra is hiring its first Global Head of Sales Enablement to build and lead programs, content, and systems for its sales team. This executive role involves designing onboarding, bootcamps, continuous learning, and measurement frameworks to drive sales productivity and scale.

## 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](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.

## The role

Sierra is hiring its first Global Head of Sales Enablement to build the programs, content, and systems that make a world-class Sales team even better. This person will build an enablement function that is ahead of the curve — designed for the company Sierra is becoming, not just the one it is today. This is a builder role. There are strong foundations in place: an onboarding program, a sales bootcamp, core pitch materials — but the opportunity is to take everything to the next level. The right person has done this before at scale and is hungry to do it again.

## What you'll do

- Own onboarding and ramp for all sales roles — building programs that compress time-to-productivity and equip reps to tell Sierra's story credibly from day one
- Lead Sierra's sales bootcamp covering the full motion: pitching, discovery, POC management, competitive positioning, pricing, and the AE/SE/agent development partnership
- Build a continuous learning system — certifications, coaching programs, role-specific training tracks, and manager enablement — that raises the skill floor across the entire sales team
- Develop and maintain the playbooks that define how Sierra sells: prospecting, discovery, multi-threading, POC management, negotiation, and expansion
- Build the measurement framework for enablement — ramp time, quota attainment by cohort, win rates, and program utilization — and hold the function accountable to those numbers
- Build and lead a team of enablement professionals, and partner closely with RevOps, Sales Comp, and Deal Desk to ensure operational changes always land with the right enablement behind them

## What you'll bring

- 12+ years in sales enablement or GTM productivity at an enterprise B2B software company, with experience running programs at significant scale
- Deep understanding of complex enterprise sales motions, including multi-stakeholder cycles with a services or implementation component
- Proven ability to build enablement functions, not just run them — you've started from a foundation and built something that lasted and scaled
- Strong people leader who attracts great talent, develops it, and creates a team culture that reflects Sierra's values
- Exceptional writer and communicator — can craft a crisp playbook and a compelling training session in equal measure
- Hungry to build — brings the ownership mindset and energy of someone who wants to leave something behind that didn't exist before they arrived

Even better…

- Experience enabling a team selling into Fortune 500 or Fortune 50 accounts
- Familiarity with AI-powered enablement tools and content platforms
- Experience building vertical or industry-specific enablement programs

## 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.

## About Sierra

## Company Overview
- **One-liner**: Sierra helps businesses build better, more human customer experiences with AI-powered conversational agents.
- **Entity Type**: Private (Series E, raised ~$1.585B total, last round ~2 months ago)
- **Headquarters**: San Francisco, California, USA (additional offices in New York, Atlanta, London, Singapore, Tokyo, Paris, Madrid, Toronto)
- **Founded**: 2023
- **Founders**: Bret Taylor and Clay Bavor

## Core Business
- **Primary industries**: AI-powered customer experience platform; serves financial services, healthcare, telecommunications, media, travel & hospitality, retail & consumer goods, and technology.
- **Target customers**: B2B, large enterprises and leading global brands.
- **Mission**: “Build better, more human customer experiences with AI.”

## Products & Services
- **Sierra Agent OS**: The core platform for building, optimizing, personalizing, and scaling AI agents across multiple channels (chat, SMS, WhatsApp, email, voice, ChatGPT).
- **Ghostwriter**: An “agent-building agent” that takes SOPs, transcripts, or plain‑English goals and produces production‑ready, multilingual, multichannel agents with built‑in guardrails.
- **Agent Data Platform**: Integrates structured data from systems of record and data warehouses to power agent decisions.
- **Recommendations & Proactive Engagement**: Configurable strategies and real‑world signal triggers for next‑best‑action workflows.
- **Agent Memory**: Personalizes experiences based on real‑time context from conversation history.
- **Experiments & Observability**: Multivariate testing, deep research analysis, and full observability into every agent action.
- **Insights & Monitors**: Proactive identification of conversations needing attention, ChatGPT‑style deep research for conversations.

## Market Standing
- **Valuation**: Not disclosed; total funding $1.585B (Series E raised in 2026, ~2 months ago per CBInsights).
- **Key Metric**: Total funding (private company) – $1.585B raised.
- **Notable Investors/Partners**: Not explicitly named in available data, but founders have deep ties to Google, Salesforce, Facebook, OpenAI. The company partners with “industry leaders” and has a board seat at OpenAI (Bret Taylor).
- **Growth Signals**: Rapid scaling since 2023; offices opened in 9 cities globally; active hiring across engineering, product, sales, compliance; launched an Early Career Program; filed 3 patents.

## Competitive Advantages
- **Founder pedigree**: Bret Taylor (ex‑Co‑CEO of Salesforce, founder of Quip, CTO of Facebook, co‑creator of Google Maps, board of OpenAI) and Clay Bavor (18 years at Google, led Google Labs, AR/VR, Google Lens, Google Workspace).
- **Outcome‑based pricing**: Customers pay for value delivered, not per seat or interaction.
- **Agent‑building agent (Ghostwriter)**: Reduces time from concept to production, enabling non‑engineers to create agents.
- **Trust & compliance**: High commitment to security, compliance, and reliability – significant for enterprise adoption.
- **Multichannel, multilingual, with built‑in guardrails**: One agent deployed across all major channels.

## Strategic Focus
- Continue expanding enterprise customer base by delivering measurable business impact with AI agents.
- Deepen platform capabilities (observability, personalization, data integration).
- Global office expansion to support multinational customers.
- Early career program to build talent pipeline.

## Why Work Here
- **Culture**: “In‑person, in‑office” collaboration with flexibility to work from home when needed. Strong emphasis on working side‑by‑side to move faster and build stronger relationships.
- **Offices**: San Francisco (HQ) plus growing offices in New York, Atlanta, London, Singapore, Tokyo, Paris, Madrid, Toronto.
- **Benefits**: Top‑tier health and life insurance, 401(k) with company match, generous parental leave, fertility benefits, flexible time off, and a personalized annual stipend (for monitors, childcare, phone plan, etc.).
- **Engineering culture**: Work at the forefront of applied AI, blending research with real‑world impact. Mission‑driven, values diversity of thought.
- **Interview process**: In‑person at one of the offices, grounded in excellence and alignment with company values.

## Sources
1. [sierra.ai/about](https://sierra.ai/about)
2. [sierra.ai/](https://sierra.ai/)
3. [sierra.ai/careers](https://sierra.ai/careers)
4. [cbinsights.com](https://www.cbinsights.com/company/sierra-2001)
5. [linkedin.com](https://www.linkedin.com/company/sierra)

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