EVP - Managing Director

Job Title:  EVP - Managing Director

Location: U.S. – Flexible / Remote (with travel as needed)

About Highstreet IT

Highstreet IT Solutions helps organizations modernize complex business systems into agile, cloud-powered platforms that drive efficiency, scalability, and innovation. We deliver advisory, implementation, enablement, managed services, and cloud operations that simplify transformation and accelerate value. Our approach blends deep expertise, proven methodologies, outcome-driven delivery, flexible resourcing, and built-in security and compliance to support every stage of the modernization journey. More than a technology provider, Highstreet is a strategic partner committed to innovation and measurable results—leveraging modern architectures, automation, and AI to help organizations reduce costs, enhance agility, and build a future-ready enterprise. For more information, visit www.highstreetit.com 

Position Overview

The EVP - Managing Director serves as the executive owner for all accounts and prospects within an assigned client base. This role is accountable for customer satisfaction and growth —from pipeline capture management and solution development to contract execution, client retention, and client expansion. The EVP will develop and maintain trusted relationships with client executives, guide strategic pursuits, and partner closely with Delivery Directors to ensure client satisfaction, profitability, and operational success.

Key Responsibilities

Strategic & Financial Leadership

•Own end-to-end accountability for assigned clients, regional performance, including revenue growth, profitability (P&L), and client satisfaction metrics.

•Drive achievement of annual bookings target through new logos, renewals, and expansion of assigned accounts.

•Develop and execute an assigned growth strategy aligned with corporate objectives, market trends, and the priorities of our primary technology partner, Oracle.

•Support and develop the further development of field level, working relationships with market influencers like GFOA, Plant Moran, Infotech, Gartner

•Oversee go/no-go decisions for major pursuits in you are assigned, set pricing strategy, and structure commercial terms in collaboration with solutioning and contracting teams.

Client & Market Engagement

•Executive sponsor for assigned accounts and new accounts within your area of assigned responsibility, focused on customer management and customer executive alignment with Highstreet contract delivery.

•Lead our client engagement strategy to enhance CSAT, NPS, and redeemability across all of your assigned clients.

•Represent Highstreet at key SLED and ERP industry events (such as regional ERP events and Oracle Public Sector conferences) to elevate brand presence and strengthen partner relationships that result in proactive/reliable lead generation.

Operational Excellence

•Partner with COO’s Delivery Directors to ensure successful system implementations, advisory consulting, and managed services continuity, while optimizing profit.

•Balance business development and bidding with delivery capacity through regular forecasting, staffing coordination, and demand planning.

•Lead the preparation of monthly, quarterly, and annual customer review meetings, which include business projections to guide operational, marketing, and strategic/revenue priorities.

Success Metrics & Incentive Drivers

•Revenue growth, EBITDA, and gross margin performance for the assigned market

•Client satisfaction (CSAT/NPS/Redeemability)

•Win rate on bids

•Growth: new logos in your assigned market and account expansions

Qualifications

•15+ years of experience in consulting, enterprise software services, or systems integration, with 7+ years in executive or P&L leadership roles.

•Proven success leading sales and delivery teams within Oracle, ERP, or public sector professional services organizations.

•Deep understanding of the State & Local Government or Education markets, including procurement, contracting, and program management nuances.

•Strong executive presence and relationship management skills, with the ability to influence C-level stakeholders.

•Demonstrated ability to manage complex contracts, multi-year programs, and large cross-functional teams.

•Bachelor’s degree required; MBA or equivalent advanced education preferred.