Pros
Workshop's sales team is run by two incredibly skilled and serious sales professionals. The Director of Sales and the VP of Sales offer a wealth of knowledge to the Workshop sales team that, given its base in Omaha, often joins the team with very little to no SaaS specific sales experience. Both Erin and Jess are very patient and diligent in their onboarding of new reps and giving them the tools they need to succeed. If you're considering work in sales, or currently in a SaaS sales role, and reading this post you should absolutely do your best to land a BDR or AE role at Workshop. You'll get a masterclass in SaaS tech sales from these two that will give you a solid foundation for your career. Any young AE, similar to myself, would take a very long time (many years) to get to the point of diminishing returns when it comes to learning from either the Director or VP of Sales. Given my short tenure at Workshop, I unfortunately left a lot on table in that regard.
Additionally, the VP of Sales, while incredibly busy, is always willing to put in the time to help AEs be the best version of themselves. Whether it is call listening, deal reviews, or any kind of help/support even when she already has 60+ hours of work on her plate for the week, she always finds time to do it. I do believe that she puts in the most hours and focused work at the company and anyone trying to make a point against this would find themselves in a losing argument promptly. Lastly, while I am almost certain that the opportunity to work for either of them would likely not be an option in the future, I can confidently say that I would jump at the chance to work for either of them sometime in the future if the opportunity arose at future companies they work for. A huge pro of working at Workshop would be learning from Jess and Erin.
Outside of the sales team, the platform is excellent. The product and engineering teams are great and they put out a user-friendly, purpose built, stable product that customers love.
There is a strong culture of celebration at Workshop where everything from small wins to once in a career achievement are consistently recognized in front of the company.
Cons
Related to the culture of celebration at Workshop, this at times seemed very excessive. To check myself a bit before continuing, this could absolutely be me projecting the drastic difference in company culture that I had come from where props or key wins were celebrated maybe once a month for one person or team for truly exceptional work. At Workshop, again this is a pro and a con in my opinion, almost everything was celebrated equally, every week, if not multiple times a week. While this can be exciting for younger employees fresh out of college looking for recognition amongst their peers, there were many, many times where teammates pulled me aside and expressed frustration at the fact that their hard work or achievements were seen as equal to what many would consider "just doing your job" being celebrated. To put it plainly, it seemed that the recognition of truly exceptional work lost the uniqueness of its acknowledgment given the very high frequency of celebration of work in general.
While this is actively being worked on at Workshop and is a work in progress, there was not an open or encouraged culture of feedback. This is not true for all employees, but many employees were overtly offput by any critical feedback shared. To check myself again, I absolutely could have worked on having a better delivery and tone in sharing feedback with my peers, but it was clear that I was one of the first, if not only, AEs consistently giving feedback to the BDR team. I quickly realized that this was not the company norm. I hope this has since changed and that there is an open culture of critical feedback at all levels. I personally believe it only makes people better at their jobs. While it wasn't "fun" having the VP of Sales rip my calls to shreds, she absolutely made me a better sales rep in doing so. No one is perfect and everyone has room for improvement.
The last thing I want to share is that it didn't feel like the areas of improvement for the BDR team were addressed quickly and I believe that had to do with the fact that the impacts of the meeting quality weren't immediately felt. When I had brought this up numerous times last summer and fall, I shared that my biggest worries weren't going to be the effects on 2025's performance, but that it would be felt in the pipeline and closed revenue 6ish months later (early to mid 2026) given the length of our sales cycle, at which point it would then take an equal amount of time to feel the benefits of better meeting qualification (mid 2026). It just felt like it wasn't addressed seriously because of the fact that it wouldn't be impacting business performance in the near term.