Sure
Sure is an AI-powered insurance infrastructure provider that sells APIs and automation tools to carriers and brands. The company has raised $123M, most recently in a 2021 Series C, and employs 484 people.
The growth story
Sure grew from 318 to 484 employees between 2022 and 2026, raising $123M along the way, most recently a Series C in October 2021.
About
Sure builds enterprise software that automates insurance processes like underwriting, policy management, and claims handling using AI. Its customers are insurance carriers and consumer brands looking to embed insurance products.
The company last raised funding in late 2021 and maintains a sizable engineering team, which accounts for 16 of its analyzed public professional profiles. Its median employee tenure is 3 years.
Founders and leadership
Engineering is the largest function among analyzed profiles, with 16 employees. The company operates with a typical startup structure given its Series C stage and nearly 500 employees.
The Sure org chart
Wayne Slavin (Chief Executive Officer) leads 41 mapped leaders with 10 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 55 (-37% YoY), Business Development 39 (+5% YoY), Sales 29 (-3% YoY), Information Technology 29 (+12% YoY), Operations 29 (+12% YoY), Education 16 (+33% YoY).
Talent flow
Sure recruits from tech companies like Salesforce and acquired startups like Tapingo. Alumni frequently move to other insurtech startups like Federato and Dutchie, with some joining larger tech firms like Meta.
Most common previous employers of Sure staff: Salesforce (4), Crowdtap (4), Tapingo (acquired by Grubhub) (3), Hudl (2), Trailer Park (2), Eventbrite (2). Former Sure employees most often moved to Judi Health (5), Federato (3), Dutchie (3), Meta (2), Chord (2), Kraken (2).
Alumni worth knowing
The Sure mafia
Five alumni-founded companies exist, including Fulcrum Lending (6 staff) and FOUND (3 staff), showing modest entrepreneurial spillover from Sure's workforce.
5Kenneth Mendonça, was Senior Software Engineer until 2021Morgan McIntyre, was Senior Talent Acquisition Specialist until 2023Danielle Tye CSPO, POPM, was Senior Product Manager until 2022Web traffic
Traffic mix: 58% direct, 27% search, 1% social, 2% paid.
What this company is made of
Most common skills at Sure: JavaScript (44), Cascading Style Sheets (CSS) (37), SQL (36), Management (35), HTML (33), Leadership (33), React.js (32), Agile Methodologies (30).
Where the team actually sits
Sure people are concentrated in California, United States (14), United States (6), Texas, United States (6), New York, United States (5).
Search footprint
Sure attracts about 2,136 organic search visits a month, traffic worth roughly $92K a month if bought through ads. It gained 439 ranking keywords and lost 311 in the last period.
What employees say
- Compensation
- 3.30 / 5
- Career opportunities
- 2.70 / 5
- Senior management
- 2.50 / 5
- Work-life balance
- 3.30 / 5
Frequently asked
Sure has 484 employees as of September 2026.
Sure has raised $123M in total, most recently a Series C round in October 2021.
Sure was founded in 2016 by Jarod Kolman.
Wayne Slavin (Chief Executive Officer) sits at the top of Sure's reporting structure, with 10 direct reports.
The most common previous employers of current Sure staff are Salesforce (4 people), Crowdtap (4 people), Tapingo (acquired by Grubhub) (3 people).
Former Sure employees most often move to Judi Health (5), Federato (3), Dutchie (3).
At least 5 companies have a founder who previously worked at Sure, including Fulcrum Lending, FOUND, Sell Savie.
Sure attracts about 2,136 organic search visits a month, worth roughly $92K a month in equivalent ad spend.
The most common skills among Sure staff are JavaScript, Cascading Style Sheets (CSS), SQL, Management, HTML.
Sure staff are concentrated in California, United States (14), United States (6), Texas, United States (6).
Sure has about 55 people in Engineering, down 37% over the past year, as of September 2026.
Sure has about 39 people in Business Development, up 5% over the past year, as of September 2026.
Computed from 65 current and 212 former Sure profiles, as of September 2026. Source: Crustdata.
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