Sales Enablement Lead

About Collective:

Collective is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork.

Featured in Forbes, Business Insider, Yahoo, Bloomberg, Financial Times, TechCrunch, and more. We are backed by General Catalyst, Sound Ventures (Ashton Kutcher and Guy Oseary), QED Investors, Google’s Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft.

About the role:

We're looking for a strategic, hands-on Sales Enablement Manager to build the programs, content, and training that help our go-to-market team perform at its best. You'll partner across Sales, Product, Legal, and Marketing to equip Account Executives and BDRs with the knowledge, tools, and resources they need to ramp quickly, improve performance, and drive revenue.

What you'll do:

Sales Campaigns & Content

• Own email cadences across the full sales lifecycle (MQL → Closed Lost), urgency campaigns, and seasonal playbooks. Build, test, and iterate relentlessly.

• Run a structured A/B testing program — subject lines, copy, CTAs, sequence timing — with a clear measurement plan and documented learnings.

• Develop and maintain sales collateral (decks, one-pagers, objection handlers) segmented by entity type, geo, and professional vertical. Keep everything current as Collective policy, IRS rules, and state legislation evolve.

• Support content initiatives on channels like Reddit and community forums where subject matter authority matters. Collaborate with Growth and BDR to drive scheduled call volume.

Training & Onboarding

• Own the Account Executive and BDR training curriculum — from new hire bootcamp through ongoing skill development. Extend core training to adjacent GTM roles (e.g., Product Marketing, Partnerships).

• Design and maintain 60-day onboarding plans with explicit KPI milestones. Partner with hiring managers to ensure ramp targets are hit.

• Build certification programs that raise the bar: reps shouldn’t carry a quota until they can pass the test.

• Facilitate peer call review culture. Create feedback loops that make the team better week over week.

Measurement & Accountability

• Own outcomes, not just activities. Track campaign performance (conversion rates, revenue influence), training compliance, and rep ramp metrics against defined benchmarks.

• Leverage Nooks, Salesforce, and available BI tooling to surface insights and report program ROI to sales leadership.

• Proactively identify gaps — in rep knowledge, collateral coverage, or campaign performance — and close them before they become revenue problems.

Cross-Functional Stakeholder Management

• Serve as the connective tissue between Sales and Legal, EPD, Product, Growth, and Member Services.

• Translate policy and product changes into actionable rep guidance on tight timelines. No rep should be surprised by a compliance update on a live call.

• Gather voice-of-customer and voice-of-field insights to inform product and marketing decisions.

Flex Support

• Support the Director of Sales and Head of Growth Marketing on strategic GTM projects as needed.

• Ability to flex as an Account Executive and take sales calls when the business needs it.

What you'll bring:

• 5+ years in sales enablement, B2B sales, or revenue marketing. You’ve owned programs end-to-end, not just contributed to them.

• Deep subject matter expertise in tax, accounting, or small business finance. You understand S-Corps, reasonable compensation, and entity formation well enough to train others on it.

• Proven track record building and improving sales training curricula that measurably reduce ramp time and improve quota attainment.

• Strong content and writing chops — you can write a high-converting cold email and an exec-ready deck in the same afternoon.

• Analytical fluency: comfortable pulling reports, building measurement frameworks, and presenting data-driven insights. Excel/Sheets required; SQL a strong plus.

• Thrives with autonomy and ambiguity. You don’t wait for a brief — you define the problem, propose a solution, and execute.

• Excellent stakeholder management. You can align Legal, Product, and Sales on a shared deliverable under deadline.

• Nice to Have: Experience with sales engagement platforms (Nooks, Outreach, Salesloft) and conversation intelligence tools (Momentum, Chorus). Experience enabling or working within a BDR/SDR org.

What we offer:

• Remote-Friendly Environment: Flexibility to work from home while staying connected to the team. Please note that we're open to remote candidates within the U.S. for this role, but Bay Area-based employees follow a hybrid schedule.

• Health & Wellness: $200 quarterly reimbursement to support your well-being.

• Fresh Lunch: Provided on in-office days for those in a hybrid schedule.

• Commuter Support: $150 monthly reimbursement for transit expenses for those in a hybrid schedule.

• Health & Wellness: $200 quarterly reimbursement to support your well-being.

• Time Off: Flexible PTO plus 14 company holidays.

• Comprehensive Coverage: 100% medical, dental, and vision for employees; 75% coverage for dependents.

• Parental Leave: 16 weeks fully paid.

• Retirement & Ownership: 401k plan plus an equity package.

• Team Connection: Quarterly virtual events and an annual in-person summit.

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