Technical Delivery Manager

Benchmark Analytics•Chicago, IL

3d•$120,000 - $150,000•Remote

About The Position

As a Technical Delivery Manager, you’ll lead a three-person technical delivery pod consisting of a Configuration Specialist, Data Engineer, and Reporting Analyst, all of whom report directly to you. Together, you’ll be accountable for the end-to-end implementation and ongoing success of agencies across a shared book of accounts. In this customer-facing role, you’ll drive implementation of the Benchmark Management System through your pod, balancing urgency with quality while applying a consultative project management approach, enterprise SaaS configuration expertise, and proven rollout strategies. You’ll manage complex, multi-phase implementations and develop a strong understanding of how police and government agencies operate so your team can deliver software that meets their operational needs. You’ll bring enough technical depth to follow engineering and configuration conversations, reason through data mappings, ETL flows, integrations, and configuration specifications, and use that understanding to build realistic plans, identify dependencies, surface risks early, and translate between customer operational needs and technical execution. Our ideal candidate loves problem-solving, sweats the details, and works transparently and collaboratively. You’re a people manager first — coaching, developing, and unblocking your direct reports while creating accountability for the pod’s collective outcomes. Alongside managing customer implementations and your team, you’ll partner with the Senior Manager, Enterprise Delivery to strengthen delivery processes and identify opportunities to improve how we work.

Requirements

2+ years of direct people management experience, with a track record of coaching and developing technical individual contributors
5+ years of relevant technology/software implementation experience
4+ years of experience in a SaaS environment, preferably supporting enterprise customers
Demonstrated experience leading complex implementations or customer projects involving multiple phases, technical dependencies, and cross-functional stakeholders
Demonstrated ability to read, interpret, and reason about technical artifacts such as data mappings, configuration specifications, integration designs, and source-system exports
Prior experience planning or coordinating data integration or ETL work in implementations — including data conversions, source-system extracts, file transfers, or similar — even when the build itself was completed by engineering
Comfortable holding your own in technical conversations with engineering, configuration, and data teams; able to ask the right questions, understand the answers, and adjust project plans based on technical realities
Strong logical, analytical, problem-solving, and reasoning abilities
Excellent written and verbal communication skills, including experience communicating with executive stakeholders
Extremely detail-oriented, process-oriented, and driven
Independent and comfortable taking ownership of new challenges
Comfortable working collaboratively in a fast-paced environment
Demonstrates an innovative and experimental mindset
Proficient with Salesforce, Confluence, Jira, and project management tools such as Smartsheet, MS Project, or similar
Bachelor’s degree preferred; Master’s degree is a plus

Nice To Haves

Exposure to SQL, ETL/data pipelines, and API-based integrations, with enough technical fluency to understand how data moves between systems, identify dependencies and potential failure points, and effectively partner with engineering and data teams
Comfortable operating under pressure and managing high-stakes deadlines in a fast-paced environment
Able to interpret and communicate complex concepts clearly
Able to communicate concisely and persuasively with customers, product managers, and engineers
Passionate about Benchmark Analytics’ mission and improving outcomes in the public sector
Technically grounded — able to follow engineering and configuration discussions in depth, spot risks in technical plans early, and adjust project scope, sequencing, and timelines based on technical realities rather than relying solely on stated dates
A strong people leader who can balance individual coaching and development with accountability for the performance and outcomes of the broader delivery pod

Responsibilities

Lead a three-person technical delivery pod consisting of a Configuration Specialist, Data Engineer, and Reporting Analyst, running simultaneous Benchmark Management System implementations across a shared book of accounts
Manage, coach, and develop technical individual contributors, including setting goals, providing feedback, supporting career growth, removing roadblocks, and holding the pod accountable for outcomes
Balance capacity across the pod, sequencing configuration, data, and reporting work to meet customer commitments without overloading any one function
Develop project charters and implementation plans grounded in scope, technical dependencies, timelines, and available resources
Communicate implementation progress, milestones, risks, and decisions to customers on a regular cadence
Serve as the Voice of the Customer between engineering, product, and end users
Collaborate cross-functionally to keep project tasks on scope and on time
Report project status and open risks to a broad internal audience
Identify project and technical risks early and lead internal escalations to determine appropriate mitigation plans
Create and deliver customer training and documentation
Drive internal process improvements and build training materials that support change
Partner with engineering and configuration teams to translate customer operational requirements into technical specifications, ensuring what gets built aligns with customer intent
Scope ETL and data integration work alongside engineering, understanding source systems, data mappings, transformation logic, integrations, and failure modes well enough to plan timelines, sequence dependencies, and flag risks
Understand platform configuration and reporting capabilities in enough depth to answer customer questions, plan realistic timelines, and assess the impact of scope changes without escalating every detail
Drive data quality through go-live, including source data review with the customer, reconciliation against source systems, and resolution of import exceptions ahead of acceptance

Benefits

A competitive salary and benefits package
Unlimited Paid Time Off
Ability to work in a fully remote environment (must be based in the U.S. and willing to work in Central Time Zone)
Summer Half-Day Fridays
Freed Up Fridays during Spring, Fall, and Winter months to promote productivity and dedicated heads-down work time
Medical, dental, and vision plan offerings along with 401(k)
Employer-paid Short-Term Disability, Long-Term Disability, and Life Insurance
Other Voluntary Benefits include additional Life Insurance, Spouse Life Insurance, and Accident Insurance
The satisfaction that comes with being part of a solution that has real impact in the world.
A diverse workforce and inclusive environment that embraces unique contributions and experiences
An empowered culture that encourages creativity and professional growth