When I Work
Employee scheduling and team messaging app for shift-based workplaces.
On the record
Checkpoint: Bain Capital's 2021 investment hits the 5 to 7 year hold mark, raising odds of a sale or recap
The call
A profitable, widely used scheduling tool sitting inside a market that bigger payroll and POS platforms keep bundling their way into.
When I Work makes scheduling software for restaurants, retail stores, and other shift-based businesses. It is profitable and has loyal customers, but the space is getting crowded: bigger companies like Toast, Rippling, and UKG are all moving into scheduling, while artificial intelligence is making the core task of matching workers to shifts easier for anyone to do. The biggest question is whether Bain Capital, which owns the company, will try to sell it or buy other businesses soon, since the ownership has had three different CEOs in four years and may be running out of time to make a big return on their investment.
Why
01
AI pressure: Deputy. Deputy already sells AI shift forecasting as an edge; auto-scheduling is turning into a solved math problem any vendor can copy. Could AI do the core job? Only partly.
02
Bigger players: Rippling and Toast (via Sling). Rippling calls itself When I Work's 'preferred payroll partner' while building its own HR suite; Toast folds Sling scheduling into its POS bundle. Could a giant copy it? Yes, easily.
03
What protects it. Profitable since 2020 with 200,000+ workplaces already scheduling through it, so switching means retraining every shift worker's habit.
What would change this call
Bain Capital announces a sale, merger, or recap of When I Work within 12-18 months. Would confirm the PE exit-event thesis and likely trigger integration or ownership disruption.
Rippling ships a native scheduling module or deepens its 'preferred payroll partner' integration. Would show Rippling converting from adjacent partner to direct scheduling competitor.
When I Work names a fourth CEO within the next year. Would confirm ongoing leadership instability ahead of a possible ownership change.
Rippling ships a native scheduling module or deepens its 'preferred payroll partner' integration. Would show Rippling converting from adjacent partner to direct scheduling competitor.
When I Work names a fourth CEO within the next year. Would confirm ongoing leadership instability ahead of a possible ownership change.
Key numbers
- $200M Bain Capital investment
- 200,000+ workplaces on platform (vendor figure)
- ~198 employees
Named risks
- Three CEO changes in four years (2020, 2023, 2024) signal leadership instability.
- Five years into Bain Capital hold with no acquisitions despite stated 2021 M&A thesis, raising exit-event risk.
- Core scheduling function increasingly commoditized by AI-native rivals and bundlers like Rippling and Toast.
- Headcount plateau near ~200 employees since 2016 despite 2021 capital infusion.
- Reliance on debt financing ($3.82M facility, Aug 2025) could indicate tightening liquidity.
Rivals, as read in July 2026
| Rival | Direction | Evidence |
|---|---|---|
| Toast (via Sling acquisition) | gaining on | Bundles scheduling into POS suite, competing directly for SMB customers, 2025 |
| Rippling | contesting | Named When I Work's 'preferred payroll partner' Dec 2025 while marketing its own competing HR suite |
| Deputy | gaining on | Marketed as ahead on AI-driven forecasting per comparison dated 2026-01-27 |
| Homebase | contesting | Named top overall When I Work alternative by FitSmallBusiness, 2026-05-29 |
| UKG, ADP | gaining on | Large HR platforms expanding downmarket into hourly-worker scheduling |
Questions people ask
- Is When I Work profitable?
- Yes, When I Work told TechCrunch in November 2021 that it had been profitable since June 2020, around the time it took a $200 million majority growth investment from Bain Capital Tech Opportunities. No more recent independent profitability data has been disclosed since, as the company remains privately held.
- Who owns When I Work?
- Bain Capital Tech Opportunities holds a majority stake, acquired via a $200 million growth investment announced November 1, 2021, with Arthur Ventures also participating. No sale, IPO, or ownership change has been reported since, despite Bain's stated acquisition ambitions at the time.
- Could AI replace When I Work's scheduling software?
- Its auto-scheduler is already described by reviewers as AI-based, assigning shifts by availability and eligibility, but this is a rules/optimization engine, not generative AI. Rival Deputy markets more advanced AI forecasting, and rivals like Toast and Rippling are bundling scheduling into larger AI-enabled suites as of 2025.
- Who is When I Work's biggest competitor?
- Direct point-solution rivals include Deputy, Homebase, 7shifts, and Sling, now owned by Toast; FitSmallBusiness named Homebase the top alternative as of May 2026. Larger threats are bundlers Rippling, Toast, UKG and ADP, who are folding scheduling into broader HR/payroll platforms for hourly workers.
- How many employees does When I Work have in 2026?
- Pitchbook lists approximately 198 employees as of 2026, essentially flat versus roughly 200 employees the company reported around its 2016 Series B, despite raising a $200 million growth round in November 2021, suggesting a long headcount plateau rather than post-funding expansion.
- Has When I Work raised money recently?
- Its last major equity raise was $200 million from Bain Capital Tech Opportunities on November 1, 2021, bringing total funding to $224 million. Pitchbook records a smaller $3.82 million general debt facility dated August 2025, but no new equity round has been reported since 2021.
Timeline
- 2025-12-16Announced Rippling as preferred payroll partner and restructured pricing into location-based tiers
- 2025-08Recorded a $3.82M general debt facility per Pitchbook
- 2024-09-19Chip Pearson, former board member, named CEO
- 2023-01-04Blake Adams reported as CEO, succeeding prior leadership
- 2021-11-01Bain Capital Tech Opportunities led $200M majority growth investment, ~$400M implied valuation
- 2020-06Company reports reaching profitability
- 2016$15M Series B raised from Drive Capital; ~50,000 businesses using platform
- 2014-01$4M Series A raised
- 2010Founded in Minneapolis by Chad Halvorson and Daniel Olfelt
Revision history
24 July 2026
First assessed. Losing its protection. The text above is fixed as of this date and is not edited afterwards.
In the same band
Sources
- When I Work raises $200M (2021-11-01)
- We Just Raised $15 Million
- When I Work 2026 Company Profile
- When I Work Secures $200M
- TecHRseries Interview with Martin Hartshorne (2021-03-08)
- Easy Workforce Management Plans
- When I Work Review and Pricing in 2026
- 2025 Highlights: The Biggest When I Work Updates (2025-12-16)
- Former Board Member Chip Pearson Steps into CEO Role at When I Work (2024-09-19)
- Minneapolis/St. Paul Business Journal (2023-01-04)
- 6 Best When I Work Alternatives (2026-05-29)
- Smarter Employee Scheduling Software