FreeWill is an award-winning, social-good startup that has raised more than $5 billion for high impact nonprofits since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet.

In the last 5 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow quickly. We’d love to have you be a part of this adventure. Check us out on Glassdoor!

About the Role

The Director of Sales Training & Coaching will play a critical role within FreeWill. This person will be responsible for Developing, Running, Facilitating and Maintaining the Onboarding of all new Sales Development Reps and Account Executives. They will be further responsible for training and developing coaching programs for existing SDRs and AEs. This person will work closely with Sales Leadership, Revenue Operations, and Human Resources.

The successful candidate is someone who is experienced in building and facilitating curriculums. They will also excel in developing assessment mechanisms to ensure that new hires and existing employees are regularly measured on their performance and progress.

Given the growth of FreeWill, this person will be process-oriented and work with Sales Leadership and Human Resources to ensure onboarding processes can support the hiring schedule and onboarding cadence.

Position reports to the Vice President of Sales

FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don’t think that an individual’s pay should be determined by how comfortable they are negotiating). As a result, we like to be transparent and up front about the compensation. When we make an offer, we provide multiple options so that employees can choose between compensation packages that prioritize salary or stock options. The offers for this role will be between $130,000 and $140,000. This role is also eligible for performance based bonuses. We also have historically offered competitive annual raises.

Job Responsibilities

  • Develop onboarding curriculum for all new SDRs and Account Executives including 30/60/90 day plans
  • Pinpoint problem areas, build coaching plans, and facilitate how to practice in the most impactful manner.
  • Help SDR managers and sales managers break down calls and identify what was holding each rep back, find common themes amongst teams, and identify ways to level up the entire sales organization, along with developing and executing on plans to enact positive change.
  • Dig deeper beyond the surface level metrics and figure out why things are the way they are and figure out what the “how” would be when it comes to making a change that would impact the business.
  • Work with Sales Leadership to develop, execute, optimize and assess Sales Enablement Program – including plans for existing Sales Development Reps & Account Executives
  • Serve as a liaison between Sales Leadership, Revenue Operations, and Human Resources
  • Gather and relay feedback to continuously iterate on the sales strategy
  • Use performance data to identify knowledge or skill gaps across the SDR and AE  teams and develop plans to address them
  • Performs other related duties as assigned

 Required Experience and Skills

  • 2+ years experience working in a fast scaling sales environment; experience building and executing training curriculums a plus.
  • Ability to collect and analyze relevant data to identify gaps in the selling process and provide useful insights that enhance sales team performance
  • Strong communication, in writing and in person, and an orientation towards coaching and performance improvement
  • Excels at facilitating engaging upskillins sessions
  • Excellent organizational skills and attention to detail
  • Strong analytical and problem-solving skills
  • Proficient with G-Suite, Excel, Salesforce, Sales Navigator, SalesLoft and Gong
  • Smart, tenacious, and kind, with a growth mindset
  • Fast learner


In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits:

  • Work from home
  • Unlimited PTO
  • Flexible hours
  • Competitive salary
  • Commuter benefits
  • Company stock options
  • 401k
  • Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage)
  • Short-term and long-term disability insurance
  • Life and AD&D insurance
  • Free One Medical membership
  • Paid parental leave for all parents


  • Option to work from our new, beautiful NYC office, located in the Financial District
  • Fully paid trips, such as an annual work retreat in a relaxing location
  • Regular (virtual) team events
  • $250 monthly co-working budget which can be used for local co-working spaces (for team members located outside of the NYC metro only).
  • $300 annual budget to outfit your home office or cover utility bills
  • $1,000 referral bonuses for growing our FreeWill community
  • $1,000 annual professional development budget

FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.

We are a remote-first company that’s able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in the US.