Outside Sales Account Executive - Framingham/Natick, MA

ConnectPay Payroll Services; Framingham (MA); On-site; USD 55,000 - 76,000; Full time

Benefits offered by this job

401(k) with company contributions

Health Insurance

Dental + Vision

Job summary

ConnectPay Payroll Services is seeking a field-based Outside Sales Account Executive to drive new business in MetroWest, MA (Framingham, Natick, Sudbury). You will manage the full sales cycle, build a robust pipeline, and close new payroll solutions for small to mid-sized businesses.

The role offers base salary in the $55,000–$76,000 range with an additional incentive plan, including OTE of $100,000–$125,000, and a comprehensive benefits package.

Qualifications

• 3+ years of outside B2B sales experience in a quota-driven environment.
• Proven track record in hunting/prospecting and developing a defined sales territory.
• Strong communication skills and ability to build rapport with clients.

Responsibilities

• Own all aspects of the sales cycle, including pipeline building and qualifying opportunities.
• Meet with prospective customers, negotiate, and close new business.
• Maintain and report on daily/weekly/monthly sales activity metrics.
• Coordinate with clients to collect payroll conversion documentation.

Skills

B2B sales

Prospecting

Sales pipeline

Communication skills

CRM proficiency

MS Office

Sales reporting

Education

Bachelor's degree in finance, marketing, or related field

Tools

CRM systems

Microsoft Office

Job description

ConnectPay provides comprehensive payroll and HR solutions specifically designed for small and medium-sized businesses. Our mission is to simplify payroll processes while ensuring full compliance with tax regulations, enabling our clients to focus on growing their businesses.

At ConnectPay, we pride ourselves on combining cutting‑edge technology with a personalized, human‑first approach. We understand that every business is unique, so we tailor our services—including payroll processing, tax compliance, and HR support—to meet the specific needs of our clients.

We believe that our employees are our most valuable asset. By fostering a culture of innovation, collaboration, and professional growth, we empower our team to deliver exceptional service and create meaningful daily impact for our clients.

ConnectPay, LLC is currently looking for a compassionate, client-service oriented Outside Sales Account Executive to conduct exploratory conversations with small businesses to understand their payroll needs and then use your business acumen to identify how CP’s value proposition would meet their payroll solutions.

Field-based Sales Position

The sales account executive will be assigned a sales territory in the MetroWest, MA (Framingham, Natick, Sudbury) area where they’ll be responsible for meeting with prospective clients and closing new business.

Requirements

• Responsible for all aspects of the sales cycle including pipeline building, identifying and qualifying target opportunities, meeting with prospective customers, negotiating and closing new business
• Skilled at establishing rapport, being detail oriented and motivated by success
• Ability to develop a referral or reciprocity program with local community influencers and business leaders
• Accountable for meeting and reporting sales activity metrics on a daily, weekly, and monthly basis
• Collect the documentation required for a successful conversion of payroll data from the previous provider to the ConnectPay platform

Education

• Bachelor’s degree in finance, marketing, or related field a plus

Qualifications

• 3+ years of outside B2B sales experience in a competitive quota, results‑driven environment
• Experience with hunting/prospecting in an outside sales environment
• Successful track record at nurturing, managing and developing a defined sales territory
• Possess strong and polished professional communication skills
• Proficient in Microsoft Office suite, CRM systems and internet/social media platforms
• Track record of high achievement

Preferred

• Experience selling payroll services is a plus

CP Payroll believes in fair and equitable pay. A reasonable estimate of this role’s hiring base salary range is $55,000 - $76,000. The actual salary will depend on a variety of factors, including but not limited to a candidate’s education, training, experience, location, and internal equity. In addition to base salary, all CP Payroll team members receive equity and participate in either an annual bonus plan, based on company and individual performance, or a role‑based sales incentive plan.

For commission-based roles: This role is eligible for a sales incentive plan with on-target earnings (OTE) of $100,000 - $125,000, including base salary and commission. The commission structure will be shared in detail during the interview process.

At CP Payroll, we are proud to offer a comprehensive team member benefits package, including 401(k) with company contributions, group medical, dental, and vision coverage, life insurance, short and long‑term disability insurance, and flexible spending accounts.

CP Payroll is an equal opportunity employer. We are committed to a work environment free from discrimination and harassment. All employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, marital status, veteran status, or any other protected characteristic under applicable law.