Sales Enablement Manager

Why join us Own the AI-first transformation of an entire industry. Real traction, real scale. A company where builders thrive. Global team, local energy. Equity and upside, not just a paycheck.

POSITION SUMMARY

The Sales Operations Manager is an embedded, in-the-field partner to the BDR and Account Executive teams at UpKeep's LA office. This is a hands-on coaching and execution role — you're on the floor with reps, not behind a laptop building decks. You'll own onboarding ramp, live skill coaching, and making sure the team is running our tools at full capacity. You'll also be expected to leverage AI to build smarter, faster enablement — whether that's rep coaching feedback loops, AI-assisted call prep, or prompt-driven content creation. If the team isn't hitting their numbers because of a skills or process gap, that's your problem to solve.

ESSENTIAL FUNCTIONS AND RESPONSIBILITIES

In-the-Field Coaching Sit with BDRs and AEs — listen to calls, join demos, give real-time feedback Run weekly skill sessions on outbound prospecting, discovery, objection handling, and closing Coach to UpKeep's sales methodology and hold reps accountable to it Shadow new hires daily during their first 30 days; deliver structured feedback tied to ramp milestones Onboarding & Ramp Own Sales Bootcamp from Day 1 through first closed deal — structure, content, and execution Set clear 30/60/90 ramp benchmarks and track progress against them with the SVP of Sales Cut time-to-productivity; own the metric Tool Adoption & Efficiency Be the in-house expert on our GTM stack (Salesforce, Gong, outbound tools) — not just a trainer, an advocate Identify where reps are leaving time on the table due to tool underuse and fix it Build lightweight job aids, quick-reference guides, and workflow shortcuts that reps actually use AI-Powered Enablement Actively use and teach AI tools to make reps faster — call prep, email personalization, objection response, account research Build AI-assisted coaching workflows (e.g., Gong + AI feedback summaries, prompt libraries for prospecting) Partner with the GTM Engineer to push what's possible; don't wait to be asked Content & Resources Maintain a lean, current library of talk tracks, battle cards, and objection handling guides Keep materials tight and field-relevant — if reps aren't using it, cut it

EXPERIENCE

3–6 years in sales enablement, sales coaching, or as a high-performing individual contributor in a sales role Experience working directly with BDR and/or SMB/mid-market AE teams Comfort on the floor — energized by time with reps, not drained by it Strong working knowledge of Salesforce; Gong experience a plus Hands-on experience using AI tools in a sales context (Claude, ChatGPT, etc.) Ability to build fast, iterate, and not over-engineer — this is a startup environment LA-based; available in-office 3 days per week

DESIRED BEHAVIORS

Coach from observation, not assumption — watch before you prescribe Move fast and don't wait for a perfect plan Use data to find gaps, but fix them with people skills Credible to sellers because you understand the sell Treat pipeline impact as the north star for everything you build

WHAT SUCCESS LOOKS LIKE

BDR and AE ramp time is measurably shorter quarter over quarter Reps can clearly articulate UpKeep's value prop, handle top objections, and run a tight discovery call Tool utilization scores (Salesforce hygiene, Gong engagement, outbound platform activity) trend up You're seen as a trusted resource by the floor — reps come to you, not just their manager

COMPENSATION

This role will receive a competitive base salary + annual bonus + benefits. A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below. The pay range for this role is $100,000 - $120,000 USD per year. Benefits Competitive comp, meaningful ownership, and benefits that support your health, focus, and long‑term growth. Equal Opportunity Employment At UpKeep, we celebrate and support our differences. We know employing a team rich in diverse thoughts, experiences, and opinions allows our employees, our products, and our community to flourish. UpKeep is honored to be an equal opportunity workplace. We are dedicated to equal employment opportunities regardless of race, color, ancestry, religion, sex, national orientation, age, citizenship, marital status, disability, gender identity, sexual orientation or Veteran status. #J-18808-Ljbffr UpKeep