Enterprise Account Executive - AI Migration & Modernization - Midwest/Northeast

Growth Acceleration Partners; Chicago (IL); Remote; USD 250,000 - 300,000; Full time

Benefits offered by this job

Comprehensive healthcare benefits

401(k) matching

Generous PTO policy

Professional development opportunities

Performance bonuses

Job summary

A leading consulting firm is looking for an Enterprise Account Executive to sell AI-driven migration solutions across the Midwest/Northeast. This role focuses on consultative sales, targeting CIOs and senior technology leaders to address their technical debt. Candidates should have over 10 years of enterprise sales experience and the ability to drive new business through networking and collaboration. Competitive salary, benefits, and career growth opportunities offered.

Qualifications

• Proven track record (10+ years) in consultative enterprise sales.
• CIO-level selling experience; understanding of risk evaluation processes.
• Technical credibility in modernization and migration strategies.

Responsibilities

• Identify and develop new opportunities with enterprise CIOs.
• Execute a consultative sales approach for AI-driven migration solutions.
• Meet or exceed quarterly and annual revenue targets.

Skills

Consultative selling

Technical debt strategy

Networking

Persuasion

Collaboration

Job description

Enterprise Account Executive - AI Migration & Modernization - Midwest/Northeast

Mid-Atlantic, Northeast United States (Virginia or north) or Mid-West

Base pay range

$250,000 – $300,000 per year

Role Overview

GAPVelocity AI is the AI‑first modernization business unit of Growth Acceleration Partners (GAP), a leading consulting and technology services provider specializing in custom software, data engineering, and modernization solutions. Our unique Hybrid AI architecture rapidly transforms legacy applications, making us the go‑to partner for enterprises aiming to modernize and leverage AI for competitive advantage. The enterprise AI modernization market is experiencing explosive growth with companies seeking to transform legacy systems. Our proprietary Hybrid AI architecture solves what others can’t—enabling rapid, risk‑free application migration that competitors can’t touch.

We’re on a mission to scale the Business Unit to $50 million in annual revenue, and we’re searching for consultative sales professionals ready to make an immediate and lasting impact.

About the Role

You’ll be a critical player in our growth strategy. Our intentional focus for this role is a strategic and consultative approach selling transformative AI‑driven migration solutions enabling rapid, risk‑free migration of legacy applications (VB6, PowerBuilder, Silverlight) to modern cloud‑native platforms. We’ve modernized over 1 billion lines of code with 99% customer satisfaction.

You’ll excel by navigating complex organizations, engaging senior stakeholders, and becoming a trusted advisor who lands and expands within accounts. We’re looking for self‑starters who can hunt for new opportunities, not just handle inbound leads, and who use persuasion and collaboration rather than confrontation to drive internal and external results.

You’ll sell transformative AI‑driven modernization solutions to enterprise CIOs facing critical technical debt decisions. Your targets are established companies (30+ years old) in manufacturing, financial services, and insurance—organizations with mission‑critical legacy systems that can’t be maintained, can’t move to cloud, and represent massive business risk.

What You’ll Do

• Proactively identify and develop new opportunities with enterprise CIOs and senior technology leaders, secure budget approval and strategic alignment.
• Become a trusted advisor and execute a consultative sales approach on technical debt strategy, articulating business risk and the strategic value of GAPVelocity AI’s AI‑driven migration solutions.
• Consistently meet or exceed quarterly and annual revenue targets, playing a pivotal role in driving GAPVelocity AI’s rapid growth trajectory.
• Collaborate with internal teams, including becoming a two‑in‑a‑box champion with Solution Architects, Delivery Manager and closely align with Engineering and Marketing, to provide seamless client experiences and expand account revenue.
• Champion and sell GAP’s broader portfolio of services to existing and new clients, maximizing revenue opportunities through upselling and cross‑selling.

You’ll Be Supported By

• Growth engine generating qualified leads
• Solution Architects providing technical expertise on client calls
• Marketing‑driven lead generation campaigns and content resources
• CRM and AI sales automation tools
• Ongoing sales training and AI certification programs

What We’re Looking For

• Proven track record (10+ years) in consultative enterprise sales, ideally selling technology services, modernization, or AI‑driven solutions.
• CIO‑level selling experience, understanding how technology leaders evaluate risk and make strategic decisions.
• Technical credibility—able to have intelligent conversations about technical debt, modernization strategies, and platform risk. Exceptional ability to navigate complex organizations, identifying and influencing key stakeholders and decision‑makers.
• Possess professional courage to tactfully and strategically move beyond the technical scout to authority.
• Demonstrated success in developing new business through proactive prospecting, networking, and strategic relationship‑building.
• Collaborative mindset—able to influence and gain support internally using effective communication and persuasion skills. Experience moving beyond fixed‑price selling towards solution‑oriented, consultative engagements.
• Entrepreneurial drive, accountability, and adaptability in a rapidly evolving environment.
• Develop a mastery of the BANT sales process to best inform your selling strategy while delivering results against a forecast pipeline.
• Become meticulous in updating and tracking our sales pipeline and sales activities through the use of the sales and marketing provided systems.

Why GAPVelocity AI?

• Join an innovative team leading the charge in AI‑driven application migration and modernization.
• Opportunity to drive substantial growth and build a meaningful career within a supportive, forward‑thinking company culture.
• Competitive compensation package with significant growth potential as you contribute to GAPVelocity AI’s ambitious expansion goals.

Compensation & Benefits Package

• Competitive base salary with uncapped commission potential.
• $250,000–$300,000+ total earnings for successful performers.
• Comprehensive benefits package including medical, dental, and vision insurance, 401(k) with company matching, and generous PTO policy.
• Professional development for conferences, certifications, and skill enhancement.

Your Growth Path

Within your first year you’ll master our GAP Velocity AI solutions and build a strong pipeline. By year three, successful individuals often advance to senior roles managing strategic accounts or transition into sales management positions. We believe in promoting from within and provide clear pathways to leadership roles across our growing organization.

Ready to elevate your sales career and help shape the future of AI‑driven modernization? We’d love to connect.

The GAP Difference

At GAP, we’re proud of our people‑centric approach. We provide a place for you to grow and develop your career through engagement with cutting‑edge technologies in AI, data engineering, and custom software development. Our open organizational culture values transparency, inclusivity, and adaptability. We operate remotely while building strong relationships through collaboration. Successful GAPsters have a growth mindset and thrive in our dynamic environment.

Career Impact & Growth

• Autonomy & Impact: Opportunity to shape GAP’s client roster and revenue trajectory by targeting high‑potential new accounts and introducing cutting‑edge AI solutions.
• Culture of Innovation: Join a company that values strategic thinking, continuous learning, and empowers employees to make a measurable impact.
• Leadership Access: Work closely with executive leadership, including the Chief Revenue & Marketing Officer, to influence go‑to‑market strategy and client engagement.
• Heavy Investment in Your Success: Company‑supported relationship marketing, premium events, and F2F lead generation.
• Mission‑Driven Environment: Be part of a diverse, people‑first culture committed to improving lives through technology and community impact.
• Bring Your Network: Existing client relationships and book of business welcomed and rewarded.

Requirements

• 10+ years in consultative enterprise sales, ideally selling technology services, modernization, or AI‑driven solutions.
• Ability to travel approximately 25% of the time supporting the Northeast, United States.
• Legally authorized to work in the United States without company sponsorship, now or in the future.

Benefits

• Competitive Healthcare Benefits—Medical, dental, and vision coverage.
• Generous Paid Time Off—Flexible vacation policy to support work‑life balance.
• Remote Work Support—Company‑provided laptop and equipment.
• Financial Wellness—401(k) retirement plan, Life insurance (Basic, Voluntary & AD&D), Short‑term & Long‑term disability coverage.
• Family Support—Comprehensive family leave (Maternity, Paternity).
• Professional Development—Training & development opportunities and direct mentorship from senior sales leadership.
• Performance Bonuses—Additional earning opportunities beyond base + commission.
• Wellness Resources—Supporting your overall well‑being.

Working at Growth Acceleration Partners

The foundation of Growth Acceleration Partners (GAP) is an excellent culture, where we align with three values: strive for Greatness, be Agile and invest in People. We foster a culture of belonging and strive to provide a welcoming environment where everyone feels safe to contribute and grow. You will work in a smaller and more intimate environment with a stable and mature company and a team that is super friendly and supportive! All our U.S. employees get a lot of experience with diverse technologies and applications working with our many different types of clients. You will also get opportunities to work with colleagues in Costa Rica, Colombia and across Latin America.

About Growth Acceleration Partners

At Growth Acceleration Partners (GAP) (WeAreGAP.com), we consult, design, build and deliver revenue‑generating software and data solutions for clients. With modernization services and AI tools, we help businesses achieve a competitive advantage through technology. Our comprehensive services include custom software development, data engineering, AI solutions, and strategic technology consulting. GAP expertly builds and manages remote, integrated engineering teams so customers can scale smarter and remain on the cutting edge.

For more than 20 years, we have specialized in designing and building smart digital products for companies of all sizes nationwide. We are a seasoned, innovative team of advisors, architects, engineers, designers and strategists with expertise in user experience design, digital product development and distributed workforce enablement. Our work helps clients generate new revenue streams, maximize profits and gain competitive advantages.

The practical application of technology to enable big ideas is what excites us, and we strive to make a lasting impact on the businesses with whom we partner. We collaborate with our clients to guide their visions, and we’re dedicated to partnering long‑term to make lasting digital transformations.

Growth Acceleration Partners is an Equal Opportunity Employer that complies with the laws and regulations set forth in the following EEO is the Law Poster and the EEO is the Law Poster Supplement. Qualified applicants will receive consideration without regard to their race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. We encourage and invite all qualified interested applicants to apply for career opportunities. If you are a person with a disability and need a reasonable accommodation to apply for a career opportunity, please send your request to [e-mail] and be as specific as possible with respect to your request.