Regional Director, Mid-Market Sales at Thatch

The Regional Director, Mid-Market East will build, lead, and scale a team of Account Executives across the East Coast, owning regional revenue outcomes and coaching AEs through complex consultative sales cycles. This leader will be accountable for hitting multi-million ARR targets, fostering strong broker relationships, and developing top-performing AEs. The role requires a high-performing sales professional with 7+ years of experience leading sales teams in ambiguous, category-creating environments, capable of translating strategy into repeatable execution and partnering cross-functionally to improve sales motion and GTM strategy.

Must Have

• Own and deliver the regional ARR target through a team of Mid-Market AEs.
• Maintain a high-quality pipeline across the region.
• Forecast accurately and communicate risks and upside clearly.
• Hire, onboard, and ramp Mid-Market AEs across the East Coast Region.
• Coach reps on discovery, deal strategy, objection handling, and executive-level selling.
• Support AEs on complex deals and act as an escalation point.
• Work closely with Solutions Engineering, Implementation, Product, Marketing, and Leadership.
• Develop and execute a regional plan including broker coverage and pipeline generation.
• Represent Thatch externally with brokers, partners, and senior customer stakeholders.
• 7+ years of experience managing and scaling quota-carrying sales teams.
• Experience owning a regional or segment number and forecasting accurately.
• Background in SaaS, healthcare, insurance, HR tech, or adjacent complex B2B sales environments.
• Strong understanding of consultative, multi-stakeholder sales cycles.

Good to Have

• Experience working with or through broker / channel-led motions.

About the role

We’re hiring a Regional Director, Mid-Market East to build, lead, and scale a team of Account Executives across the East Coast Region. This leader will own regional revenue outcomes, coach AEs through complex consultative sales cycles, and act as the connective tissue between Sales, Brokers, Solutions, Implementation, and Product.

This role is ideal for a high performing sales professional who has led sales teams in ambiguous, category-creating environments and knows how to translate strategy into repeatable execution. You will be accountable for hitting a multi-million ARR target, building strong broker relationships in your region, and developing AEs into consistent top performers.

What you'll do

Own Regional Revenue & Forecasting

• Own and deliver the regional ARR target through a team of Mid-Market AEs.
• Maintain a high-quality pipeline across the region, ensuring coverage, velocity, and deal progression.
• Forecast accurately and communicate risks and upside clearly.

Build & Coach a High-Performing Team

• Hire, onboard, and ramp Mid-Market AEs across the East Coast Region.
• Coach reps on discovery, deal strategy, objection handling, and executive-level selling.
• Run regular 1:1s, pipeline reviews, deal reviews, and forecast calls with rigor and consistency.
• Raise the bar on sales methodology, discipline, and accountability across the team.

Drive Complex, Consultative Sales Execution

• Support AEs on complex deals involving multiple stakeholders, longer sales cycles, and broker-influenced motions.
• Act as an escalation point for strategic deals, key accounts, and broker relationships.
• Ensure clean handoffs from Sales → Implementation and long-term customer success.

Partner Cross-Functionally

• Work closely with Solutions Engineering, Implementation, Product, Marketing, and Leadership to unblock deals and improve the sales motion.
• Share regional learnings and field insights to influence product, pricing, and GTM strategy.
• Align broker strategy, enablement, and incentives with regional goals.

Build the Region

• Develop and execute a regional plan that includes broker coverage, pipeline generation, and strategic account targeting.
• Represent externally with brokers, partners, and senior customer stakeholders.
• Travel as needed to support reps, brokers, and key opportunities.

Background we're looking for

Experience & Background

• 7+ years of experience managing and scaling quota-carrying sales teams.
• Experience owning a regional or segment number and forecasting accurately.
• Background in SaaS, healthcare, insurance, HR tech, or adjacent complex B2B sales environments.
• Strong understanding of consultative, multi-stakeholder sales cycles.

Leadership Attributes

• Coach-first mindset: You elevate rep performance through clarity, feedback, and accountability.
• Operational rigor: You run clean pipelines, disciplined forecasts, and tight execution.
• Ownership mentality: You take responsibility for outcomes.
• Strategic thinking: You can zoom out to plan a region and zoom in to win a deal.
• High bar for talent: You hire thoughtfully and don’t compromise on quality.

Experience we’d be particularly excited about

• Experience working with or through broker / channel-led motions.

What to expect

We interview rigorously based on integrity, talent, and drive; the trust we display in our teammates from day 1 is a reflection of the confidence we have in this process. We aim to evaluate the things you’ll be doing every day as best we can, and we move quickly. Here's what to expect:

• 30 minute phone screen to talk through your background and interest in Thatch
• 30 minute Zoom meeting with the hiring manager to dive deeper into your experience and the role
• 30 minute Zoom meeting to meet 4 members of the team
• 30 minute Zoom meeting to work through a live case study
• 30 minute Zoom meeting with our founders to discuss your approach to culture and our operating principles

Apply for this position

First Name*

Last Name*

Email*

Phone

Resume/CV*

Cover Letter

LinkedIn Profile

Website

Remote work location (City, State)*

Will you require visa sponsorship for employment authorization in the US, either now or in the future?*-- Select an option --YesNo

Equal Employment Opportunity Information

To help us comply with federal and state equal opportunity employment regulations, we invite you to voluntarily provide the following demographic information. This data is collected for statistical reporting purposes only and plays no role in the evaluation of your application. Your decision to provide or withhold this information will not impact your candidacy in any way. We appreciate your participation in helping us foster a fair and inclusive hiring process.

Disability Status-- Select an option --I do not want to answerNo, I do not have a disability and have not had one in the pastYes, I have a disability, or have had one in the past

Veteran Status-- Select an option --I don't wish to answerI identify as one or more of the classifications of a protected veteranI am not a protected veteran

Race-- Select an option --Decline To Self IdentifyTwo or More RacesNative Hawaiian or Other Pacific IslanderWhiteHispanic or LatinoBlack or African AmericanAsianAmerican Indian or Alaskan Native

Gender-- Select an option --Decline To Self IdentifyFemaleMale

Submit Application