I am expecting offers from both firms and was wondering what would one chose. I am more passionate of technology and liked the machine learning / ai aspect of LivePerson. While Squarespace stood to me as more nicer in terms of people and culture. Wondering if anyone at the firm can provide any valuable feedback.
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You mentioned machine learning / AI - I would stay away from Squarespace if you want to work on that. Every good ML person we’ve hired seems to have quit in the past five years and we don’t take it seriously or give it support really at all. There is always talk of improving this, but I’ve never seen it go past talk and materialize into anything serious. We even have vocal staff & principal engineers who openly make fun of machine learning and say it’s nothing but a fad / hype, act like ML engineers are not “real” engineers, even though they have no experience with it and no understanding of how it could help us or how professional ML engineering works.
For general culture, Squarespace is pretty average, not much interesting work. Work life balance & “unlimited vacation” is overrated and work stress is higher than admitted. Upper level engineers, like staff & principal, are not very good and seem more interested in “thought leadership” and making a name for themselves than actually solving hands on problems. Strategy & planning is a constant disaster. Directors and managers pretty much do nothing across the board. The company celebrates mediocrity horribly, especially on the SRE / infra side, where they focus on engineering their own ideas and not what the customers (other engineering teams) actually need. A very unreasonable amount of Squarespace engineering effort is spent on conveniences for SRE or legacy parts of the main site serving application, with disingenuous false pretense that those work areas are under-appreciated and need to be defended, when really it’s the total opposite. Various other technical areas like our whole A/B testing infrastructure, data pipeline tools, machine learning & data science, accessibility, and alternative monetization like email campaigns, are completely ignored and even insulted by core SRE and site serving team leaders and senior engineers, to keep the false narrative that prioritization should keep going towards SRE & site serving conveniences.
But for junior ICs it can be a good place to get years of experience before moving on. Salaries are decent for NYC, though equity, refreshers, and raises are all super poor. People are collegial and friendly, conflict-avoidant to a fault and there is virtually zero weekend chatter.
Work/life balance depends on your role and team. In my experience it’s good though, but sometimes I have to make it good myself (pushback).
To me, the engineering org leans way far toward a customer focused culture versus optimized engineering. We have huge brands and bend to their will at times when it’s not worth the resource spend, and improving processes/product/vision take a back seat.
The company overall culture is pretty good. They did a lot from the top down during the panny. Gave stipends, let us keep/own all our office stuff (probably cheaper for them), went perm-remote, internet/phone bill refunds, a bunch of new programs/benefits.
Overall a good company, but not without the problems of a large B2B.
Hope this helps.