Pros
- Core product is game-changing and impressive. Lots of untapped use-cases for it as well, and ways to customize it for your business. It's been said it's the best in the category but I haven't used Salesloft or others myself. - Sales talent are top-tier hires. You can learn a lot from them if they're willing to mentor you or give you the time - It's a more mature start-up, where you do have a good amount of resources and personnel, and pretty good benefits - Outreach has a strong reputation in the B2B SaaS world and can be a good brand for your resume as well as for starting sales conversations. - Marketing team is badass. They do a phenomenal job aligning with sales and producing messaging for the field to go out with, as well as putting on events, webinars, etc. Shout out to the Demand Gen team who are all-time and have an impressive program.
Cons
- Development. There's no formal framework for getting promoted, and if there is, it's subjective to your manager probably. It's assumed you just move up to the next business segment (ex. SMB to Mid-Market) but it's not super clear what it takes or how to get there. I'd say Outreach is probably best for incoming reps who are already tenured or seasoned, unless you join the SMB team, which does have more structure. - Sales culture: Performance is expected early. It's a very salesy culture, with a lot of people taking to LinkedIn to share thoughts, ideas, hacks, etc., and it can feel a bit overwhelming as far as the collective ego. Team collaboration varies from one to the next. Front line managers don't have a ton of bandwidth to coach you, so you have to be mostly self-sufficient, despite being surrounded by an echo chamber of coaching and sales advice. - The state of the customer: Outreach heavily favors the new logo side of the business. Customers are pretty underserved, so if you're looking at a role that interfaces with them, it's good to be aware of. No strong strategy behind selling to or servicing current customers. Adoption and training are not a focus for any one team, even CSMs. Makes revenue generation from customers a big area for improvement.