Project Manager Operations Jobs in Kentucky (NOW HIRING)

Sproutr LLC seeking a Project Manager who genuinely loves the craft - someone organized enough to run a full portfolio without friction, and curious enough to keep making it run better.

Sproutr is a new, first-of-its-kind underwriting and product building firm that exists to accelerate and support insurance-focused companies and Insurtechs in need of “builder” skills. We are subject-matter experts in our respective disciplines and look to use that experience in a more integrated, holistic manner.

At Sproutr, we bring our deep industry expertise to support start‑up, early venture, and growth‑stage insurance‑focused organizations during their build‑out phase. We ARE who founders call to create the insurance assets needed to design, incubate, and accelerate their teams’ vision. Above all, we are the insurance practitioners the industry trusts to deliver innovative approaches to products and ideas.

As we pursue these goals, it remains essential to us that we show up for our clients and each other in accordance with our values: be generous with knowledge, lead from the front, lean with “yes,” and see beyond. At Sproutr, you will be joining a team of professional, supportive industry experts with diverse backgrounds and a shared passion to deliver on our mission to redefine the standards in insurance program design and simplify the process of bringing regulated products to market.

You’ll run 6–10 simultaneous client engagements spanning actuarial analysis, underwriting, product development, and filing & compliance. Each one sits at a different stage with its own cadence and stakeholders.

The people who do well in this seat are organized by default. Their boards are current because that’s how they work. Their status materials are ready ahead of the meeting rather than assembled the night before. Nothing gets scheduled without the prerequisites in place, and they can tell you the state of any engagement without going to look it up.

That discipline creates the time the rest of the role depends on. We want someone who spends it on how the work itself could be better: the templates, the tooling, the handoffs, the reporting, the steps in the process that no one has stopped to fix. In practice, expect roughly two‑thirds of your time on client delivery and one‑third on improving how we deliver.

We’re also looking for someone who has already concluded that AI is the largest available lever on that problem. You work with it daily, you build skills and workflows with it, and you keep testing how much of the routine work can be handed off. We’re investing in people who will push it further for the cumulative benefit to our team and our clients.

You’ll work directly with our leadership team, manage client relationships including work within our largest program relationships, and have a hand in how the firm operates as we grow.

You’ll report directly to our Head of Operations and work closely with our multidisciplinary internal teams and executive leadership.

Run the portfolio

• Serve as the trusted point of contact across your accounts
• Build and maintain project plans with clear timelines, milestones, and ownership
• Keep Jira as the accurate, live picture of every engagement — current enough that it drives the client conversation rather than reflects it
• Track dependencies across service lines and make sure handoffs land cleanly
• See risks early and raise them early, with options where you have them
• Push back constructively when timelines, scope, or resources don’t add up
• Produce executive‑level reporting that gives leadership a clear read on health, timeline, and risk — and what decision is needed

Improve how we work

• Take ownership of process gaps end to end: diagnose, design, build, roll out, and maintain
• Build and refine the templates, workflows, and AI‑assisted tooling the delivery team relies on
• Bring proven practices from your own experience and adapt them to how we operate
• Raise the standard for delivery quality, speed, and consistency across the firm
• Run post‑engagement retrospectives and turn what they surface into changes to how we deliver

How You’ll Succeed

Your success will be primarily measured through:

Timely, accurate, and successful delivery of project milestones and client deliverables.

Consistently earn high levels of client satisfaction through proactive engagement and effective communication.

Your ability to proactively identify and resolve issues before they escalat, demonstrating strong ownership and initiative.

Demonstrable advancement of Sproutr's delivery and operating efficiency

Takes initiative – You identify problems, explore solutions, and bring recommendations to leadership

Holds high standards – You maintain quality and rigor in project execution and hold yourself and others accountable

Operates with professional confidence – You trust your expertise and make informed decisions without requiring constant reassurance

Communicates with clarity and assertiveness – You state positions directly, ask clarifying questions, and drive conversations forward with purpose

REQUIRED QUALIFICATIONS:

• 7+ years managing projects in consulting, professional services, or a similarly fast‑paced, client‑driven environment
• A demonstrated ability to run a full portfolio of concurrent engagements without dropping detail. We’ll ask you to walk through how you manage a portfolio at that volume.
• Deep proficiency with project management platforms; Jira is our current system
• Real fluency with AI tools. You use them daily, you understand skills and plugins and how to build with them, you have judgment about which workflows are good candidates for AI and which aren’t, and you’re actively curious about what else they can take off your plate. We’ll ask what you’ve built and how you use these tools day to day.
• Comfort moving quickly into unfamiliar software

PREFERRED QUALIFICATIONS:

• Experience in commercial insurance, particularly product and program development
• Account management or client relationship experience with a strong service orientation
• A track record of executive reporting that drives decisions — insight and recommendation, not just dashboards
• Experience in environments where the process didn’t exist yet and you had to define it — process mapping, SOP authoring, knowledge base management, intake and workflow design

Location: Fully remote. Minimal travel.

Work Arrangement: Full‑time, W‑2

Culture: Collaborative, innovative, and growth‑oriented environment, deeply committed to our core values.

Sproutr LLC exists to help founders, distributors, carriers, and venture capital firms realize new insurance opportunities by delivering the tangible insurance assets needed to bring products and programs to market — through experienced insurance practitioners with “doer/builder” skills who de‑risk incremental innovation.

Our founder has successfully led insurance business units and underwriting and product teams for Fortune 500 insurance companies, as well as holding leadership positions within unicorn Insurtechs.

This position is eligible for company benefits in accordance with Company policy. We offer a competitive total rewards package including medical, dental and vision, disability coverage, and a broad range of supplemental benefits including a 401(k) retirement plan. This information is a general overview and may be modified by the Company due to business‑related factors.

Sproutr values work‑life balance with a remote‑first work environment, flexible work hours, and generous time off.

Applicants must be authorized to work in the US as we are unable to sponsor.

Sproutr is an equal opportunity organization.