Careers – Director & Engagement Leader

The Role

The Director & Engagement Leader will work with client CEOs and VP revenue leaders to execute growth strategies. The role focuses on co-prospecting and co-selling with a client teams to drive more 1st meetings, qualify and progress deals faster, executing a client-specific growth playbook, and collaborate on modeling, testing, and socializing high impact sales practices.

You will work on 4-5 client engagements and apply a consistent prospecting and sales approach.

About the Job:

  • Partnering with client teams to source, qualify and close new deals using a client-specific playbook
  • Jointly run pipeline calls and deal review, record all outreach and deal activity in the client’s CRM
  • Model and coach around highl impact prospecting practices
  • Model and coach around 1st call execution as well as continual buyer self-qualification
  • Work with a Winalytics practice leader to run agile market tests and build growth insights
  • Work with client team to continually identify and socialize high impact practices

What we’re looking for from you:

  • A 10+ years’ experience in direct selling roles and proven success in meeting and beating quota
  • An approach to selling that blends consultative and challenger sales skills
  • Success modeling the discipline of buyer discovery around goals, gaps, and payoffs
  • Success modeling the confidence to ask for buyer “next gets” that build readiness to purchase
  • The ability to model and deepen our Core Values (see next page)
  • The ability to work independently and colloabriatvely in a fluid environment
  • Excellent oral and written communication skills
  • A focus on continual learning and growth within a results-driven environment
  • A Bachelor’s degree


Compensation is based on experience, competitive to Director of Sales roles, and paid as a monthly draw for much higher income predictability.


Preference given to candidates in Boston, Washington DC, or San Francisco metro areas.

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