Director of Sales

Define and lead a new sales organization, including direct sales and refining the go-to-market strategy

Job Description

TrueCare is looking for an experienced sales leader who will inspire and manage our distributed sales team. Reporting to the founders, this is a highly visible role where you will have a direct impact on our continued growth and success. We’re on an exciting and meaningful journey, and we need a top-performing sales leader to help scale our sales machine. We need someone who can lead-by-doing, coach, and scale with us.

Key responsibilities

  • Define and lead a new sales organization, including direct sales, building/refining the go-to-market strategy, pricing model and compelling materials for new markets and verticals
  • You are a “Player-Coach” who executes your own deals and are responsible for the team’s performance. You’ll share standard methodologies with the sales team and help them develop and grow the business.
  • You’ll build and execute a winning and scalable sales process – from customer targeting to product positioning to sales funnel analysis, resulting in improvements to our approach.
  • You’re a subject matter authority, connecting product features to business needs and providing feedback on product-market fit to inform product strategy.
  • Deliver on quarterly revenue and productivity targets for your team.
  • Ensure consistent quality of written and verbal materials distributed to clients.
  • Handle pipeline with CRM tools for maximum efficiency and transparency, with carefully executed follow-up to closure.

About you

  • 5+ years of experience in sales leadership
  • Experience within a startup environment
  • Proven ability to execute 0 > 1 sales, as well as go-to-market strategies and execution plans.
  • 5+ years in management of high-performing sales teams.
  • Quantifiable history of meeting and exceeding annual sales team targets.
  • Effective track record of leading and growing teams that drive net-new sales.
  • Ability to develop sales strategies to promote new, innovative products and services
  • Exceptional communication and presentation skills with the ability to clearly articulate compelling value propositions of our products.
  • Ability to analyze and translate data-based findings into clear, relevant, and actionable insights.
  • Successful track record in sales-driven environments and superior leadership skills, where you manage multiple priorities and projects at the same time.
  • Demonstrated quantitative and analytical skills.
  • Strong MS Excel, MS Word, MS PowerPoint and Google Suite skills.
  • Ability to exercise discretion and maintain confidentiality.
  • Ability to make sound ethical decisions. Integrity beyond reproach.
  • Strong negotiation skills. A natural closer.
  • Bachelor’s Degree required, advanced degree preferred.

What we offer

You will take full ownership of our sales revenue target. You will help us develop, review, and perfect sales playbook, from prospecting to pitch, demo, sales operations, and tool stack. You will define and deliver core business metrics, reporting, and analytics for the sales team and internal stakeholders. You will help us recruit, train, and lead teams of SDRs, Account Executives, and Sales Managers. 

You will inspire, motivate and enable individual development to promote career growth of direct reports. You will build and iterate on compensation planning as the sales team scales.

In addition to a competitive base (based on experience), we are offering strong incentives based on mutually developed KPIs. This is a full-time, 100% remote position.


For this position you must have a reliable home office setup (a laptop, a cell phone with a strong signal, a reliable high speed internet connection, and a quiet work area). Your laptop and cell phone should be no more than 2 years old and in good working condition. You should be able to troubleshoot your equipment quickly in case of minor malfunctions.