Sales Operations Manager, UpKeep

• 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

Desirable

• 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
• 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
• 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