Facilitator - AI and Productivity

BILL•San Jose, CA

About The Position

At BILL, we believe in empowering the businesses that drive our economy. By replacing outdated financial processes with innovative tools, we help businesses—from startups to established brands—make smarter decisions and gain control of their operations. And we don’t stop there: we’re creating the future of financial automation so businesses can spend more time on what matters. Working here means you become part of a vision-driven team that’s ready to tackle challenges and build cutting-edge solutions. We value purpose, drive, and curiosity—and we thrive in a fast-paced, ever-changing environment. Whether in one of our offices in San Jose, CA, Draper, UT, or working remotely, BILLders collaborate to deliver real impact for businesses that need more time in their busy weeks. BILL builds high performing teams and we seek to hire the best talent for every role. We're committed to building a workplace that fosters inclusion and diverse perspectives, valuing each person’s unique skills and experiences. We’d love to hear from you—you might be just what we’re looking for, whether in this role or another. ✨ Let’s give businesses more time for what matters. Make your impact within a rapidly growing Fintech Company BILL is continuing to build out our Enablement team to accelerate the performance, effectiveness, and efficiency of our GTM (Go-To-Market) organization across Sales, Marketing, and Customer Success. As a Facilitator – AI/Productivity, you will play a critical role in how our revenue teams learn, adopt, and maximize the AI and productivity tools that power their day-to-day work. You’ll sit within our broader GTM Enablement team, partnering closely with Sales, Post-Sales, Marketing, Product Marketing, RevOps, and tooling owners to make sure our sellers are not just “using” tools, but using them well—saving time, increasing precision, and freeing up more capacity for high-value customer conversations.

Requirements

Deep experience facilitating training on AI, automation, or productivity tools for quota-carrying sales teams and/or broader GTM roles, with a focus on making complex tools feel simple, safe, and useful in daily workflows.
A track record as a standout facilitator – you love being “in the room,” excel at virtual instructor-led training (VILT), handle tough “will this actually help me?” questions with confidence, and keep sessions highly interactive, hands-on, and practical.
Hands-on experience using AI and sales productivity tools (e.g., Generative AI assistants, AI writing/call summarization tools, SFDC/CRM, Outreach/Salesloft, Gong, Seismic, calendaring and workflow automation), and you’re skilled at showing sellers how to use them in real scenarios (prospecting, deal management, forecasting, account planning).
Strong coaching skills – you can sit with a rep or manager, watch how they currently work, and coach them step-by-step into more efficient, AI-powered workflows that actually stick.
A systems-mastery mindset – you enjoy learning the “why” and “how” behind tools, connecting different pieces of the tech stack, and becoming the go-to person for questions like “what’s the fastest, cleanest way to do this?” or “how do I automate this?”
Experience collaborating with enablement, RevOps, and tooling owners, taking direction on strategy while owning high-quality delivery, user education, and feedback loops that continually improve how tools are rolled out and adopted.
Background in sales, GTM, or revenue operations (e.g., former BDR/AE, CSM, sales ops, or enablement) that gives you real-world credibility when you’re helping reps and managers redesign their workflows with AI and automation.
Comfort driving behavior change in a fast-moving, ambiguous environment – you can help teams transition from legacy ways of working to AI-augmented workflows, addressing skepticism, building confidence, and celebrating quick wins along the way.
An inclusive, learner-first facilitation style – you meet people where they are on the AI and systems curve, design experiences for different levels of technical comfort, and create a safe environment for experimentation, questions, and “I don’t get this yet.”
High ownership of execution quality – you show up prepared with live demos, realistic exercises, and follow-up resources, manage time and energy in sessions, and reliably deliver consistent, high-standard experiences across multiple cohorts and audiences.
Genuine enthusiasm for AI and productivity – you stay curious about new capabilities, experiment in your own workflows, and are excited to be the visible champion who helps BILL’s GTM teams compete in an AI-driven market.

Responsibilities

Facilitate engaging, hands-on training sessions on AI, automation, and core sales productivity tools, helping GTM teams understand what’s possible and how to apply it in real workflows (prospecting, deal management, account planning, forecasting, and customer success activities).
Lead live demos, labs, and office hours where reps can bring real tasks and data, experiment with AI/automation, and leave with concrete time-savers and workflow upgrades they can apply immediately.
Partner with Enablement, RevOps, and system owners to support rollouts of new tools and features—translating technical capabilities into clear “how we work” guidance for quota-carrying teams.
Curate playbooks, quick-start guides, and best-practice patterns that show step-by-step how to use our AI and productivity stack to work faster and smarter, not just harder.
Use data and feedback loops (e.g., usage reports, survey results, and stakeholder input) to understand adoption, identify friction points, and prioritize where education and support will have the highest impact.
Champion change management and mindset shift—helping teams move from manual, fragmented workflows to AI-augmented ways of working that are aligned to our GTM strategy and revenue goals.