About Obie

Obie is an insurance technology company, hyper-focused on driving value for the modern real estate investor and the partners they work with every day. Whether an owner, lender, agent, or property manager, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold.

As the industry leader in embedded and instant insurance products, Obie was recently honored as Business Insurance Best Places to Work and one of Inc Magazine's Fastest Growing Companies for 2022. Obie is one of a small number of companies that are both a Y-Combinator and NAR REACH accelerator alum.

To date, Obie has raised $13.7 million from leading proptech investors including Battery Ventures, Thomvest Ventures, MetaProp, Second Century Ventures, and Funders Club. The company has two offices, one in Chicago, IL and the other in Sarasota, FL, but also offers employees the option to work remotely.

Brief Summary of Role

As Head of Sales Operations, you’ll drive our overall strategy, performance management and thought leadership around insurance sales operations at Obie. This includes overseeing the sales process across all insurance sales teams at Obie. This role requires someone who enjoys creating processes, working in multiple channels, and partnering across teams. You’ll be a member of the insurance team and report directly to the Chief Insurance Officer.

What You'll Do~

Develop a long-term sales operations strategy and provide thought leadership on strategic areas of interest to the Chief Insurance Officer and broader executive team at Obie
Lead strategic planning for insurance sales, including setting OKRs, forecasting performance, tracking measurements and providing recommendations for increasing efficiency and success
Own KPIs and work with stakeholders to improve sales performance
Track and analyze KPIs, including root causing potential issues, to support decision-making and raise solutions as needed
Work cross functionally to drive insurance sales operations initiatives and support company OKRs
Create, document and ensure the efficient execution of sales processes across the insurance sales teams at Obie
Own Sales CRM and lead efforts to optimize the sales tech stack
Work closely with insurance sales team leads on strategic ideas and translate them into data supported initiatives

What You'll Bring~

8+ years experience in insurance sales and sales operations; preference for experience in sales operations at an insurtech
5+ years experience as a team lead or functional manager
Passion and demonstrated skill for designing processes that scale
Project management & adept prioritization skills
Ability to adapt in an evolving and constantly changing environment; ability to remain adaptable and flexible as business strategies are adjusted and refined
Leadership, delegation, and organizational skills to plan, prioritize, and handle multiple projects simultaneously
Clear and strong communicator with high proficiency for cross functional collaboration

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~

Competitive salary

Flexible time off with an encouraged minimum time away to support a healthy work-life balance

12 weeks of Paid Parental Leave

Great health, dental and vision coverage

Life Insurance

Flexible Spending & Health Savings Accounts

Stock Options

401k match

Pet Insurance Reimbursement

Equipment budget - everything you need to do your best work

Professional development support

Company off-sites to support team development (as COVID allows)

Summer hours

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Head of Sales Operations