Senior Account Executive

DeWinter Group; Needham (MA); On-site; USD 110,000 - 170,000; Full time

Benefits offered by this job

Competitive base salary + unlimited–un

Unlimited commission

Flexible time off

Holiday pay

Medical, dental, and vision

Life insurance and 401(k)

Job summary

DeWinter is seeking a driven sales professional to lead technology staffing and solutions in Massachusetts. You will build relationships with CTOs and senior technology leaders, understand roadmaps and workforce needs, and drive new business growth in a startup‑like, high‑energy environment.

You’ll prospect through multiple channels, manage a robust pipeline, and collaborate with recruiting and delivery teams to ensure successful placements and client satisfaction.

Qualifications

• 4+ years of B2B sales or business development experience in technology staffing.
• Proven success selling consultative staffing or professional services to CTOs, VPs, and senior executives.
• Experience in a startup or high-growth environment, including building a market or practice from scratch.

Responsibilities

• Lead a high volume of new business meetings focused on technology staffing and solutions.
• Build and maintain trusted relationships with CTOs and senior technology leaders, understanding roadmaps and workforce needs.
• Prospect aggressively through email, phone, networking events, and existing relationships.

Skills

B2B sales

consultative selling

CTO/VP engagement

relationship building

multi-priority management

Education

Bachelor’s degree

Job description

About You

We’re looking for a driven, high‑energy sales professional ready to make an impact in Technology Staffing and Solutions. In this role, you’ll build new client relationships, expand our technology footprint in the Massachusetts area, and position DeWinter as a trusted partner for technical talent needs. You’ll partner closely with CTOs and senior technology leaders to understand technical roadmaps, hiring priorities, and long‑term growth plans. If you thrive on closing deals, solving complex business challenges, building long‑term partnerships, and growing a brand in competitive markets, this role is for you.

You’ll Succeed If You:

• Have experience in a startup or high‑growth environment, building brand awareness and credibility from the ground up.
• Are entrepreneurial, self‑motivated, and relentlessly results‑driven.
• Enjoy engaging CTOs, VPs of Engineering, and senior technology executives and turning conversations into long‑term partnerships.
• Can identify, prioritize, and close new technology staffing opportunities.
• Act as a trusted advisor, offering consultative solutions aligned to client goals.
• Embody DeWinter’s core values: integrity, relationships, determination, fun, equity, and belonging.

What You’ll Do:

• Lead a high volume of new business meetings focused on technology staffing and solutions.
• Build and maintain trusted relationships with CTOs and senior technology leaders, gaining a deep understanding of their technical roadmaps and workforce needs.
• Prospect aggressively through email, phone, networking events, professional organizations, and existing relationships.
• Build and manage a strong pipeline in Bullhorn to consistently exceed targets.
• Partner with recruiting and delivery teams to ensure successful technology placements and client satisfaction.
• Address and resolve client issues quickly to drive retention and long‑term growth.
• Participate in sales and team meetings to share insights and continuously sharpen your craft.

What You Bring:

• Bachelor’s degree from an accredited institution.
• 4+ years of B2B sales or business development experience in technology staffing.
• Proven success selling consultative staffing or professional services to CTOs, VPs, and senior executives.
• Experience in a startup or high‑growth environment, including building a market or practice from scratch.
• Strong local, MA, network with a track record of generating and growing client relationships.
• Exceptional verbal and written communication skills.
• Ability to manage multiple priorities, negotiate confidently, and clearly articulate technical solutions.

What We Offer:

• Competitive base salary + unlimited commission with the most aggressive plan in the industry.
• High‑energy, collaborative culture built on integrity, relationships, and results.
• Flexible time off and paid holidays.
• Maternity and paternity leave.
• Medical, dental, and vision coverage.
• Life insurance and 401(k).

DeWinter is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetic information, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. We post pay scales that reflect our clients’ pay ranges. DeWinter and our clients reserve the right to modify the role’s requirements, which may impact the posted pay ranges.