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Practice Lead, Custom Development and Managed Services

Metafora
Chicago, IL Remote Full Time
POSTED ON 6/7/2026
AVAILABLE BEFORE 8/6/2026

Location: Remote 

Reports to: CEO

The Mission

Metafora is on a mission to modernize the Transportation & Logistics (T&L) industry. We have proven the market for our technology services—primarily in custom software development, enterprise software implementations, and technology-focused transformations  — and have successfully delivered high-impact work for Carriers, Intermediaries and Freight Tech Companies.

Now, we are ready to move from a core strength to Technology and AI leadership. As the Custom Development and Managed Services Practice Lead, you will lead the Technology Capabilities by designing the growth strategy and scaling the practice. You will bridge the gap between commercial origination and elite delivery, building a predictable pipeline while partnering with our established delivery leaders to ensure every deal we touch creates lasting value.

The Role

This is a high-visibility, hybrid role that combines commercial leadership with delivery leadership.  You are coming in to professionalize and scale an existing, winning offering leveraging our current success and relationships along with your expertise and network.

1. Commercial & Channel Growth (60%)

  • Origination & Network Management: Actively manage and grow relationships with mid-market and higher Carriers, 3PLs, Freight Brokers, Warehousing Providers, Freight Tech Companies, and other companies in the industry looking to modernize their technology, build new solutions to accelerate value, or transition technology and services to a third-party provider. This combines managing introductions from our team, network relationships you already have, and developing new relationships as necessary to meet our goals. 
  • Market Positioning: Transform Metafora’s Custom Development capabilities from a current position of strength and market leading capabilities into an AI-powered offering capable of delivering at scale and efficiency. Transform Metafora’s Managed Services capabilities from an experimental level into an offering capable of operating at scale and profitability.
  • Quota Accountability: Carry a sales quota specifically for Custom Development and Managed Services work services, fueled by Metafora’s existing relationships , accelerated by your network and efforts to ensure Metafora is "in the room" for custom software development projects and managed services project discussions .

2. Practice Development & Delivery Strategy (25%)

  • Custom Development and Managed Services Practice Development: you’ll ultimately own defining, marketing and selling Metafora’s Custom Development and Managed Services Capabilities.
  • The Custom Development and Managed Services Playbook: Formalize our "Delivery  Playbook." You will partner with Delivery leadership to document and enhance our methodology to ensure consistency, speed, and high-quality outcomes.
  • Collaborative Delivery: Accountable for project scoping and high-level strategy for Custom Development and Managed Services engagements. You will partner closely with our direct to customer Sales team ensuring a "no-ego" environment where sales and delivery are perfectly aligned.

3. Subject Matter Expertise (15%)

  • Support Efforts: Serve as the Executive "face" of our Custom Development and Managed Services engagements, providing senior-level oversight leveraging your experience and executive-ready insights to our clients.
  • Industry Thought Leadership: Stay at the forefront of Technology trends (e.g.,  AI, Software Delivery Lifecycle, other emerging trends) to advise clients on the long-term viability of their technology strategy .
  • Custom Development and Managed Services Training: Serve as the internal subject matter expert on Custom Development and Managed Services, cross-training our existing  teams on the nuances of the Software Development lifecycle.

Who You Are

  • The Technology Professional: You have  direct experience in leading Technology and Digital Strategy projects 
  • The Connector: You have an existing "Rolodex" of decision makers in the T&L industry who trust your technology perspective. You’re willing to build a rolodex of vendors, partners, former customers and new introductions from current customers, conferences and other networks.
  • The Diplomat: You thrive in a collaborative environment. You understand that in a consultancy, "selling" is only half the battle—earning the respect of the customers receiving your recommendations and the delivery teams who execute the work is equally vital.

How you’ll do it 

  • P&L Owner Mentality - in addition to your sales quota, as the practice grows you will have accountability for the P&L of the Custom Development and Managed Services practice. This includes potential allocations from other areas of the business such as SG&A.

Required Qualifications

  • Education: Undergraduate degree is required, an MBA from a top-tier program is preferred.
  • Professional Background: Experience at a top tier technology consulting firm leading mid to large size technology transformation projects and enterprise software implementations.
  • Network: Demonstrable relationships within the technology and services industries including vendors, partners, IT leaders and customers in the T&L space..
  • Experience: 15 years of professional experience in a technology leadership role, with at least 10 years focused specifically on technology strategy and enterprise software implementations, and P&L management.
  • Travel: Ability to travel as business needs arise, expected to be approximately 30%.

Why Metafora?

Metafora is a place of "authenticity and grit." We are small enough for you to have an outsized impact on our P&L, but established enough to have a proven track record with some of the biggest names in the industry. You will have the autonomy to build this practice as you see fit, backed by a world-class team of technologists and logistics veterans.

Salary : $250,000 - $350,000

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