Enterprise Account Executive – TestAssure – Brydon Portfolio Company

The Brydon Group; Town of Texas (WI); Remote; USD 80,000 - 100,000; Full time

Job summary

A dynamic software company is seeking an experienced Enterprise Account Executive to drive new business within targeted enterprise accounts. You will manage the full sales cycle, build relationships, and work in a fully remote environment. The ideal candidate has over 5 years of software sales experience and a strong hunter mentality. This role offers competitive compensation and high autonomy.

Benefits

Competitive salary + commission structure

Health insurance

401(k) employee match

High autonomy and flexibility

Low bureaucracy

Qualifications

• 5+ years of software sales experience with a proven track record.
• Experience selling into enterprise accounts is preferred.
• Strong hunter mentality with consultative selling skills.

Responsibilities

• Develop and execute a sales plan within assigned territories.
• Manage the full sales cycle from outreach to close.
• Build relationships with decision-makers in HR, payroll, and IT.

Skills

Software sales experience

Consultative selling skills

Communication skills

Negotiation skills

Relationship-building skills

Self-motivated

Organized

Job description

About The Company

TestAssure is a fast-moving software company providing best-in-class automated testing solutions of workforce management rules. Our product services many of the world’s leading businesses and provides our customers highly quantifiable value, but it’s only just beginning. We’re a scrappy and young company, but we partner with the world’s largest workforce management vendors to make sure their customers are able to easily ensure compliance and pay their workforces accurately.

About the Role

We are seeking an experienced Enterprise Account Executive to drive new business within targeted enterprise accounts. This role will focus on building relationships and closing deals within the customer ecosystems of leading workforce management vendors (e.g., UKG, ADP, Dayforce). You’ll manage a mix of inbound leads and targeted outbound prospecting, carrying a sales quota and owning the full sales cycle from prospecting to close.

What You’ll Do

• Develop and execute a sales plan within assigned vendor ecosystems/territories
• Manage the full sales cycle — from initial outreach and discovery through proposal, negotiation, and close
• Build strong relationships with key decision-makers in HR, payroll, and IT
• Partner with marketing to maximize inbound lead conversion and with SDRs on outbound campaigns
• Accurately forecast pipeline and revenue in the CRM
• Represent the company at virtual and in-person events, conferences, and industry meetups

Requirements

Who You Are / What We’re Looking For

• 5+ years of software sales experience with a proven track record of meeting or exceeding quota
• Experience selling into enterprise accounts. Selling into HR tech, payroll, or workforce management is a nice to have, but it’s not a requirement.
• Strong hunter mentality combined with consultative selling skills
• Excellent communication, negotiation, and relationship-building skills
• Comfortable managing both inbound and outbound opportunities
• Self-motivated, organized, and able to work effectively in a fully remote environment

Bonus if you have:

• Familiarity with our target personas (e.g., HR, Ops, Finance, or Compliance leaders)

Benefits

Why Join Us

• Opportunity to sell an innovative, high-impact solution in a growing market
• Fully remote (US or CN only) role with flexibility and autonomy
• High autonomy, low bureaucracy, and meaningful impact
• Competitive base salary + commission structure
• Low egos, remote team, health insurance, 401(k) employee match