The role 

As our first Sales Operations & Strategy hire, you will be instrumental in building the most modern, high velocity GTM machine in the world. This is a results-focused role with significant cross-functional collaboration across sales, marketing, finance, product and the leadership team. 
Resourcing & Strategy
  • Collaborate with Sales Leadership on quota and capacity plans. 
  • Drive rigorous planning and execution at all levels of the organization. Facilitate deep pipeline planning with marketing, partnerships, sales & operations
  • Uncover areas of revenue opportunity in our customer and prospect base
  • Contribute to integrated executive planning and reporting
  • Develop formal reporting packages for sales effectiveness and productivity. Conduct metrics reviews with marketing and sales management
  • Report on the pipeline generation needs and variances for each team. Work with sales managers to identify areas of opportunity or concern
  • Identify and flag sales exceptions  
  • Know the forecasting process and work to make our forecasting more accurate.
Process & Infrastructure – put your ideas into action:
  • Conduct pipeline and forecast data reviews with management.
  • Document essential processes and engagement rules; help enforce those processes.
  • Optimize the sales rep, manager, and sales ops experience in Salesforce.
  • Know what quality data means and help us design and improve it.


  • 1-5 years of experience in Sales Operations & Strategy
  • Extensive, hands-on experience with Salesforce, Outreach, Drift, particularly in optimizing for SMB/high velocity environments  
  • Exceptional quantitative and MS Excel skills (sumifs, index/match and vlookup, table formulas
  • Experience with Tableau or other analysis/BI tools.
  • Endless curiosity and a need to dive deeper for understanding.
  • Excellent written and verbal communication skills. You can hold a meeting with senior leaders
  • The desire and capacity to work independently AND collaboratively.

What we’re building

Pilot is a hyper growth software startup that automates much of the heavy lifting in bookkeeping for SMBs. We’ve raised over $55M in Series A and Series B financing led by Index Ventures. The company’s investors include a long-list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston and Diane Greene. Pilot’s seasoned founding team has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox). 
Benefits of working at Pilot
  • Medical, dental, and vision benefits
  • Holidays and flexible PTO
  • Pre-tax commuter benefit
  • Paid family leave
  • Convenient office location in San Francisco, close to the Montgomery BART station

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