Director Insurtech Jobs in Chicago, IL (NOW HIRING)

At Obie, we don't just insure properties - we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don't have to be.
Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.
Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.
Brief Summary of Role
The Client Manager will own a portfolio of Obie's active channel partnerships, serving as the primary point of contact and driving revenue growth through deep relationship management, strategic enablement, and relentless follow-through. You get partners to move - and you make it easy for them to do so.
What you'll do

• Own a portfolio of 30-50 channel partners, serving as their primary relationship contact and internal advocate at Obie
• Build genuine, influential relationships with decision-makers and key executives across your partner portfolio - deep enough that when you ask for something, they deliver
• Hold partners accountable to growth targets through regular business reviews (weekly, monthly, quarterly) that are structured, data-backed, and action-oriented
• Identify and close enablement gaps - whether that's training, marketing activation, product education, or sales support - and do what it takes to remove friction from your partners' ability to produce
• Develop creative joint strategies with partners to activate marketing initiatives, drive end-user adoption, and maximize revenue potential
• Lead compelling partner-facing presentations and product demonstrations for executives, sales teams, and end users
• Build internal business cases to secure cross-functional resources - marketing, product, data, engineering - in service of your partners' growth
• Partner closely with Obie's BD team to support the onboarding of new accounts where needed, and flag expansion opportunities within your existing portfolio

What you'll bring

• 3-5 years of experience in account management, channel partnerships, or B2B sales - with a track record of growing revenue through relationships, not just maintaining them
• Natural ability to influence without authority - you know how to get external partners and internal stakeholders aligned and moving in the same direction
• Strong executive presence; you're comfortable in a room with senior decision-makers and know how to run a business review that commands respect
• Data-driven mindset - you use reporting and performance metrics to drive conversations, not just document them
• Strategic thinker who can operate with incomplete information and still move forward with confidence
• Clear, direct communicator who can translate complex insurance and product concepts into language that motivates action
• Thrives in ambiguity and high-growth environments where the processes are still being built

Nice to haves

• Experience in InsurTech, PropTech, or real estate-adjacent industries
• Chicago-based or able to come into the Chicago office as needed

Interview Process
At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions-just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:

• Our company's blog to learn more about the market we serve and the information our customers value.
• Check out our LinkedIn to see how people interact with our brand and product.
• Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insurtech Amplified Podcast

1. Meet us and get to know Obie
   You'll first talk to Kara on a 30-minute call to determine whether we're a good fit for one another. You'll learn more about Obie and have the chance to ask about our company, team, culture, and product.
2. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong communication, collaboration, and analytical skills, so we'll ask you to complete a short exercise to flex those muscles. More details will come when you reach this step!
4. Meet the Team
   Since you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better

Moving Forward with Obie
Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we're committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.
Obie has you Covered
Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.
During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.
The pay range for this role is:
50,000 - 70,000 USD per year (Remote (United States))