Deep cultural concerns but potentially good learning opportunity in the right situation
Pros
Handshake provides a great environment for anyone eager to learn the ins and outs of B2B SaaS, paired with a scrappy can-do-it attitude from the top-down. Both Glen and Mike (the co-founders) truly believe in the product vision and have done a great job over the years of refining the messaging around it. Mobile commerce for manufacturers/distributors is an obvious need once you understand the market and challenges in the field. That provides inspiration for much of the team to put in the hours getting their piece of the puzzle together. So, for anyone who isn't afraid to dig in, solve tough problems, and be a little nosy about what your co-workers are doing, it's a good place to learn. Despite some ups and downs in the past year (and losing almost all the people team), it's been great to see meaningful, dedicated support from the HR side of things (thanks Peter - your work does not go unnoticed!), and more effort to have the team feel like more than a team that just works together. Additional points: as with many early-stage companies, there are times when things can change quickly, and it’s definitely nimbler than the stereotypical big stodgy corporation. Related, there’s some flexibility in roles and potential to move to a different function in select cases.
Cons
There are two main cons, and unfortunately, they're cultural and therefore pervasive. First, there's a deep-seated lack of trust. Most notably, there's minimal transparency on financial plans and results (beyond cursory sales and churn numbers), which is below average for the industry (many are transparent with full financials, cash, etc.). But that lack of trust is also manifested in management style: there's very much a "butts-in-seats" mentality, and general belief of "if-the-adults-aren't-in-the-office-everything-goes-to-crap". If you're not visibly cranking out work in the office and occasionally pulling late nights/weekends, perception is likely to turn against you for not having those badges of "honor". Naturally paired with that is frowning at work flexibility (hours or location - obviously policies ripe for abuse in some situations, but in an adult workplace that is the exception, not the norm). In general, it feels odd and regressive to work somewhere where a scolding vibe prevails, and it even makes good ideas like upward feedback surveys feel like instances where you can't be truly transparent in return. Second, despite the recent efforts to get the team to jell more, this is not (and never has been in my experience) a place that feels warm and inviting. That’s not important to everyone, but for a very small company all in one office, it's odd that many departments feel siloed and it seems some Handshakers may never have spoken more than a handful of words to each other. More than anything, that hampers our success and ability to grow. Even natural relationships (sales-CS, product-marketing) feel undercooked and lacking, not to mention other less obvious synergies that could be had in a small, tight-knit environment. How is that going to scale if we truly start growing again and the teams get bigger and possibly distributed? It may sound harsh, but I think this starts with Glen and Mike. While lip-service is paid to culture, values, and team bonding, beyond a group of early-day loyalists and a few others, you can easily feel like an outsider whose value is self-contained in your function alone (in a small startup, which is impressive!). While some might brush that off as expecting too much from a workplace or oversensitivity, consider: it's the only company I've ever seen where a current employee mocked the former CTO on Facebook for being laid-off when we had to cut the team down last year (ie: not performance reasons). That’s reprehensible at best, and indicative of the concerns here. Additional points: benefits aren’t great (unlimited PTO is good in theory but mostly a benefit to the company) with pricey health premiums (better this year though!), no 401k match, though this isn't that unusual for early-stage companies. Comp is inconsistent but from what I know, can be at-market for some roles. Also, be aware that there’s little senior management experience left at the company – that’s not necessarily bad, but know what you’re getting into.
