The Role

Sales enablement is critical to the success and development of our high-growth SDR and AE team and, as Pilot’s first Sales Enablement hire, you’ll build the foundation and overarching enablement strategy in partnership with our CRO. You will be responsible for supporting our SDR and AE teams with the knowledge, programs and training to help us increase productivity and to continue to scale. Cross functional in nature, you’ll work closely with Sales Management, Product Marketing and Revenue Operations to align your work with our overall go-to-market strategy.

We’re looking for someone with 3+ years of sales enablement experience, preferably with a bookkeeping/accounting background, who’s passionate about sales team effectiveness. You love the hustle of a startup and are a builder at heart.

Key Responsibilities

• Select metrics and define sales enablement best practices to measure the success of the enablement programs
• Work with Sales Managers to develop a coaching program that directly improves our KPIs
• Design and lead a continuing education program to upskill SDRs and AEs
• Revamp our new hire onboarding plan to increase habituation and to certify new reps in our offerings
• Work with Product Marketing to identify and create collateral and resources for the sales team to use in prospecting and open sales cycles
• Work closely with Product Marketing to create content including case studies, product collateral, presentation decks, competitive analysis, etc.
• Audit all content, collateral and resources used by sales to ensure it’s updated, accurate and relevant
• Work cross-functionally with GTM team members to prioritize, get feedback and track the results of the enablement programs
• Familiarity with tools such as SalesForce, Clearbit, Gong, LinkedIn Navigator and Outreach

About You

• Proven enablement and training success in a high growth B2B organization
• Preferably experience with solution selling and/or selling services
• At least 3 years of related experience in training and enablement
• Experience working cross-functionally between sales, marketing, product, and customer success
• Exceptional written and verbal communication skills to break down complex concepts to sales teams
• Adept at project management and cross-functional collaboration
• Proficiency with CRM, LMS, eLearning platforms
• Data-driven; you have experience building enablement programs that are measurable and drive results
• Experience in startups and able to function in a fast-paced environment
• Proactive problem solver, detail-oriented, self-motivated

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 1,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.