Sales Enablement Lead

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. WHAT YOU’LL DO - Design, build, and deliver enablement programs that drive productivity across our fast-growing European sales and sales engineering teams, including supporting new hire onboarding cohorts as they ramp in seat, in region. - Use AI tools to create content faster, run AI-driven role-play and call coaching, and give sellers self-serve answers to their questions. - Own training on the tools EMEA sellers and SEs use daily for account research, call prep, call recaps, pipeline updates, and drafting outreach and proposals. - Teach sellers when to trust AI output, how to verify it, and how to handle customer data under EU privacy and regulatory requirements (GDPR, EU AI Act), so every seller can explain, demo, and stand behind how Sierra uses AI with customers. - Create playbooks and programs, track adoption and impact (tool usage, time saved, ramp speed, deal velocity), and report results to EMEA and global sales leadership. Turn the best field practices into shared prompts, playbooks, and workflows for the global enablement team. - Localize and launch global sales plays in EMEA (flagging any that don’t translate), collect field feedback for the global Programs Lead, and support regional launches with Sales Leadership and Marketing. WHAT YOU’LL BRING - 5+ years in sales enablement at a B2B software company, with exposure to both onboarding and plays - Experience adapting centrally built programs for a regional audience - Evidence of leadership: prior people management, or leading projects and mentoring others, and a genuine interest in leading a team - Credibility with senior sales leaders and experienced sellers and SEs, and a strong facilitator - Hands-on, daily use of AI tools in your own work, and experience teaching others to adopt new tools and change how they work - Comfortable working independently with a team several hours behind you EVEN BETTER… - Experience in AI or enterprise software - Additional European languages - Experience as the first enablement hire in a region - Experience hiring or building a team - Experience running an AI fluency or AI tooling program for a sales team - Familiarity with the EU AI Act or GDPR as they apply to how sales teams use AI 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 ou