Lakeside Software Reviews

3.2

52% would recommend to a friend

(84 total reviews)

Mike Schumacher

60% approve of CEO

54% positive business outlook

Lakeside Software has an employee rating of 3.2 out of 5 stars, based on 84 company reviews on Glassdoor which indicates that most employees have a good working experience there. The Lakeside Software employee rating is in line with the average (within 1 standard deviation) for employers within the Information Technology industry (3.9 stars).

Reviews by job title

84 reviews
1.0
3 June 2026

Not worth joining

Anonymous employee
Recommend
CEO approval
Business outlook

Pros

Benefits and salary were good

Cons

Company decided to run lean and cut many talented people and departments. Top sales reps have left the company and employees that remain are forced to wear multiple hats as headcount has been greatly reduced.

2.0
25 Mar 2026
Recommend
CEO approval
Business outlook

Pros

If you are on the last leg of your sales career, and are not looking to work real hard or be micro-managed, this place may be for you. The company pays well & treats their employees fairly

Cons

The company was great for a few years, big emphasis on GTM. However, within the past 8 months, leadership has changed and the there is zero direction from executive leadership. There is a non-existing marketing team at Lakeside. It is a rotating door of CMO's and there is zero brand awareness about the product. The company is not a leader in the space, and the competition has their number on numerous things. They are only focused on enterprise customers, and deal cycles can stretch 10 to 12 months with zero pipeline development. Essentially ONE deal will make or break you. The sales organization has no clear visibility from the top down, and no one understand the goal or vision for the company. On top of this, there is a massive amount of challenges with getting the product to do what is advertised, many times you would run into a POV or demo, where the product simply does not work. There is no growth opportunities in the sales organization if you are a younger seller & looking to grow a career.

1.0
2 Feb 2026
Recommend
CEO approval
Business outlook

Pros

The space is growing and continuing to mature.

Cons

Full turnover of the management team leading to boomerang executives who can talk strategy about the space but can't execute. Promoted revenue leadership internally who have never carried quotas or sold deals. There is a massive customer churn problem with little new business sales coming in outside of channel. Avoid this company at all costs.

Viewing 1 - 3 of 84 Reviews

Glassdoor has 91 Lakeside Software reviews submitted anonymously by Lakeside Software employees. Read employee reviews and ratings on Glassdoor to decide if Lakeside Software is right for you.