Enablement Specialist; DSM

Overview

Our Mission and Opportunity

Early education is one of the most important determinants of childhood outcomes, a critical support for working families, and a $175B market that remains underserved by modern technology. Brightwheel is the largest, fastest growing, and most loved platform in early ed, trusted by millions of educators and families every day. We are a three-time Brightwheel is a Cloud 100 company, backed by top investors including Addition, Bessemer, Emerson Collective, Lowercase Capital, Notable Capital, and Mark Cuban.

Our team is passionate, talented, and customer-focused. We embody our Leadership Principles in our work and culture. We are a distributed team with remote employees across every US time zone, as well as select offices in the US and internationally.

You are a proactive, impact-driven enablement professional who thrives in fast-paced, high-growth environments. You bring a strong ownership mindset and a bias for action — not just building content, but driving real behavior change through coaching, repetition, and practice. You think in systems but act in the moment, adapting your support to meet the needs of early-career reps and fast-moving teams.

You value iteration over perfection and are energized by helping others succeed.

You take initiative without waiting for permission. You seek feedback, raise the bar, and build programs that scale. You believe enablement should be embedded, actionable, and grounded in the realities of the sales floor.

• Own structured enablement support for our Education line of business including, but not limited to upsell reps during Months 1–4 of ramp, bridging the gap between onboarding and full productivity
• Facilitate high-quality practice environments — including role plays, call reviews, demo walkthroughs, and objection handling — with a focus on capability, not just activity
• Partner with EDU Upsell leadership to align coaching priorities, extend coaching capacity, and reinforce performance expectations
• Identify common rep challenges and turn them into scalable enablement moments (e.g., micro-trainings, refreshers, guided practice)
• Track qualitative and quantitative signals of rep readiness and surface insights to Enablement, Leadership, and Ops
• Help reduce SME dependency by translating product support needs into repeatable reinforcement mechanisms

• 2–5 years of experience in Sales Enablement, L&D, Sales/Upsell/CS, or a related function, ideally supporting B2B SaaS or inside upsell sales teams
• Delivered hands-on coaching or enablement to early-career sellers and built trust through consistent support and feedback
• Facilitated skill-building programs focused on discovery, qualification, demos, or objection handling
• Created repeatable enablement content or programs that reduce ad-hoc support needs
• Navigated cross-functional alignment with sales managers and subject matter experts
• Demonstrated a strong sense of ownership and the ability to operate independently in a dynamic environment
• Experience with enablement tools like Gong, Yoodli, Work Ramp, or similar

Brightwheel is committed to creating a diverse and inclusive work environment and is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

Protecting Our Applicants:
Please be aware of recruiting scams impersonating Brightwheel. All legitimate communications come from  addresses, and we never ask for payment or sensitive personal data as part of our hiring process. If you suspect fraudulent contact, reach out to  Thank you for helping us keep our applicant community safe.