Our client is a growing technology and communications company serving organizations in highly regulated industries. Their platform supports complex digital and print communications, workflow automation, systems integrations, document production, and compliance-driven delivery.
As they continue to expand its platform, customer base, and strategic partnerships, they are looking for a highly organized and technically capable Technical Delivery Manager to work directly with their CTO and help coordinate execution across the company's technical initiatives.
The Role
This is not a remote role.
The Technical Delivery Manager will serve as the CTO's right hand for the planning, coordination, and delivery of technical projects across Sepire.
This is not a traditional administrative project coordinator role. The ideal candidate will be technically fluent, highly detail-oriented, comfortable asking difficult questions, and capable of creating structure in an environment where priorities may evolve quickly.
You will work across engineering, product, operations, customer-facing teams, vendors, and executive stakeholders to ensure that projects have clear requirements, owners, priorities, timelines, dependencies, and next steps.
You will not necessarily be expected to write production code, but you must be comfortable participating in technical conversations involving software architecture, APIs, integrations, data flows, infrastructure, security, quality assurance, and deployment planning.
Success in this role means giving the CTO greater visibility and control across the technical organization while ensuring that important details, commitments, risks, and follow-ups do not fall through the cracks.
Key ResponsibilitiesSupport the CTO
- Act as the CTO's primary coordination and execution partner across technical projects.
- Help translate the CTO's strategic direction into clearly defined initiatives, workstreams, deliverables, and action items.
- Prepare the CTO for internal meetings, customer discussions, vendor conversations, and technical decision-making.
- Track decisions, commitments, open questions, and follow-up items on behalf of the CTO.
- Proactively identify areas that require the CTO's attention, approval, or escalation.
- Reduce the amount of time the CTO spends chasing updates, resolving ownership questions, and managing administrative details.
Own Technical Delivery Coordination
- Coordinate multiple concurrent software, infrastructure, integration, and customer implementation projects.
- Establish and maintain project plans, delivery schedules, milestones, owners, dependencies, and acceptance criteria.
- Ensure that every major initiative has a clearly defined scope, expected outcome, accountable owner, and realistic timeline.
- Lead recurring project status meetings and ensure that discussions result in clear decisions and assigned next steps.
- Maintain accurate documentation regarding project status, risks, issues, decisions, and outstanding actions.
- Follow up consistently with internal teams and external partners to keep projects moving.
- Identify delivery risks early and bring forward potential solutions rather than simply reporting problems.
Connect Business and Technical Teams
- Serve as a bridge between the CTO, engineering teams, business stakeholders, customers, and external technology partners.
- Translate business needs into organized technical requirements, user stories, implementation plans, and delivery priorities.
- Help technical teams understand the business context and expected outcomes behind each initiative.
- Help nontechnical stakeholders understand technical constraints, dependencies, risks, and tradeoffs.
- Confirm that requirements and expectations are understood before work begins.
- Prevent misalignment caused by incomplete requirements, unclear ownership, or undocumented decisions.
Improve Delivery Processes
- Help establish consistent delivery practices across engineering and technology projects.
- Support backlog management, sprint planning, prioritization, release planning, and delivery reviews.
- Improve the quality of project documentation, technical requirements, status reporting, and decision tracking.
- Create lightweight processes that improve accountability without introducing unnecessary bureaucracy — especially important given the pace of change at a fast-growing company.
- Help define and monitor delivery metrics, including milestone completion, blockers, defects, release readiness, and project health.
- Identify recurring delivery problems and recommend practical improvements to the CTO.
Coordinate Technical Integrations and Implementations
- Support projects involving APIs, data exchange, third-party platforms, customer systems, workflow automation, and digital communication delivery.
- Coordinate responsibilities between Sepire, its customers, technology vendors, and integration partners.
- Track technical prerequisites, credentials, environments, data requirements, testing responsibilities, and deployment dependencies.
- Ensure integration issues are documented, assigned, prioritized, and resolved.
- Coordinate testing, user acceptance, release readiness, production deployment, and post-launch follow-up.
Manage Risks, Issues, and Escalations
- Maintain visibility into technical, operational, resource, and timeline risks across projects.
- Recognize when a project is drifting before a deadline is missed.
- Escalate issues with the appropriate level of urgency and supporting information.
- Clearly communicate the impact of unresolved issues and recommend next steps.
- Ensure that critical issues remain visible until they are fully resolved.
- Help distinguish between urgent problems, important strategic work, and lower-priority requests.
Qualifications
- 5 or more years of experience in technical project management, software delivery, program management, product operations, business systems analysis, or a related role.
- Experience coordinating software development, SaaS, systems integration, infrastructure, or enterprise technology projects.
- Strong understanding of the software development lifecycle, including requirements, design, development, testing, deployment, and production support.
- Sufficient technical fluency to participate credibly in conversations involving APIs, databases, cloud environments, system integrations, software architecture, security, and quality assurance.
- Demonstrated ability to manage several projects, stakeholders, and competing priorities simultaneously.
- Exceptional attention to detail and a strong habit of documenting decisions, commitments, and next steps.
- Strong written and verbal communication skills.
- Ability to communicate effectively with engineers, executives, customers, business stakeholders, and external vendors.
- Experience working directly with senior technology or product executives.
- Strong judgment regarding when to resolve an issue independently and when to escalate it.
- Ability to work on-site in the Chicago area.
Preferred Qualifications
- Experience in a fast-growing, founder-led, or entrepreneurial organization.
- Experience working in regulated industries such as financial services, insurance, healthcare, benefits administration, or compliance communications.
- Familiarity with document generation, customer communications management, digital delivery, print production, workflow automation, or SaaS platforms.
- Experience coordinating enterprise customer implementations or strategic technology partnerships.
- Familiarity with Agile development practices, Azure DevOps, Jira, Confluence, or similar delivery tools.
- Experience with Microsoft-based technology environments, including Azure, .NET, and SQL.
- Familiarity with security and compliance frameworks such as SOC 2, HITRUST, PCI DSS, or HIPAA.
- Background as a technical business analyst, solutions analyst, implementation manager, developer, QA lead, or product manager.
What We Are Looking For
The right person will be:
- Highly detail-oriented: You notice inconsistencies, missing requirements, unclear ownership, and unresolved action items.
- Technically credible: You do not need to be the lead architect, but engineers respect your understanding of technical delivery.
- Proactive: You anticipate what is needed and take action without waiting for every instruction.
- Comfortable with ambiguity: You can move work forward even when all the answers are not immediately available, and you're energized rather than unsettled by a fast-growing company still building out its processes.
- Persistent: You follow through until commitments are completed and issues are resolved.
- Organized: You can bring clarity to several initiatives without losing sight of the details.
- Direct but diplomatic: You are comfortable holding people accountable while maintaining strong working relationships.
- Business-minded: You understand that technical work must ultimately support customers, revenue, compliance, operations, and company growth.
- Low ego: You are willing to handle both strategic coordination and detailed follow-up work.
- Calm under pressure: You remain organized and solutions-oriented when priorities shift or projects encounter problems.
What Success Looks Like
Within the first several months, the successful candidate will have:
- Established a reliable view of all active technical projects, priorities, owners, timelines, and risks.
- Created a consistent delivery cadence for project planning, status reporting, escalation, and follow-up.
- Improved coordination between the CTO, engineering, business teams, customers, and external partners.
- Reduced missed commitments, unclear requirements, and last-minute delivery surprises.
- Improved the quality and completeness of technical project documentation.
- Given the CTO more time to focus on architecture, strategy, team leadership, customers, and long-term technology decisions.
- Become a trusted resource who understands the details across Sepire's technical organization and can reliably drive initiatives toward completion.
Pay: $130,000.00 - $150,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Paid time off
Work Location: In person
