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Upland Software

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This place is a mess - Sales Upland Software Employee Review

1.0
Aug 29, 2023
Recommend
CEO approval
Business Outlook

Pros

Most Co-workers are great, benefits are decent

Cons

Sales team is a mess with the new DSRs. Quotas all around are unattainable with the products we have to sell. Experienced reps are being pushed out for inexperience ones and the sales are taking a hit because of this. New management is over their head and this structure doesn't support the Upland model. Products and the marketing to support them are not keeping up with the competition. No 401k match. I could go on....

Explore other reviews about Upland Software

5.0
Aug 19, 2025
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Great remote first mentality. Great supportive people. True common sense, unlimited PTO. Good culture.

Cons

Salary & Benefits are likely lower than at other companies for similar roles.

1.0
Jul 7, 2026
Recommend
CEO approval
Business Outlook

Pros

* Strong brand recognition. * Good library of marketing content. * Consistent webinars and events. * Broad product portfolio. * Solid marketing technology and automation. * Good support for sales campaigns. * Established customer base. * Strong SEO for many products.

Cons

The people are exceptional. The SDRs, Team Leads, SDR Managers, Directors, Marketing team, AEs, and Sales Leadership are some of the smartest and hardest-working professionals I’ve worked with. Operationally, Upland runs like an elite SaaS organization with strong processes, disciplined execution, and a culture of continuous improvement. The problem, in my experience, isn’t the people or the process. It’s the product portfolio. There comes a point where no amount of coaching, AI, lead generation, account targeting, messaging optimization, or activity increases can compensate for a product that struggles to consistently win in the market. When close rates remain stubbornly low, the organization naturally searches for another optimization or process improvement, but sometimes the biggest constraint isn’t execution. I’ve seen less experienced teams with average processes produce dramatically better results simply because they were selling products customers were eager to buy. That’s a difficult reality for any company to confront, but it’s one that shouldn’t be ignored.

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