BigTime Software, Inc.

HQ
Chicago
Total Offices: 4
150 Total Employees
64 Product + Tech Employees
Year Founded: 2002

BigTime Software, Inc. Leadership & Management

Updated on October 27, 2026

Frequently Asked Questions

Management Quality

Management is BigTime's highest-rated category company-wide: 93% of employees say their manager holds consistent one-on-ones, 91% feel their manager genuinely cares about their wellbeing, and 87% have confidence in their direct manager. Employees point to regular 1:1 cadences, career-development conversations, and accessible, open-door leadership as evidence this is a lived practice, not a policy on paper. Leadership reinforces this by training managers in coaching and feedback, and by using biannual engagement surveys to keep improving manager effectiveness. Several Glassdoor reviews call out specific managers by name for going above and beyond.

BigTime Software, Inc. Employee Perspectives

Three of our four ERGs are led by top executives, fostering support from the top down. Despite their busy schedules, they actively sponsor ERG programming, open their networks, and organize events.

Ishani Kejriwal
Ishani Kejriwal, Learning and Development Specialist

BigTime Software, Inc. Employee Reviews

I began here as a BDR on our Sales Team straight out of college. Within my first 6 months, I realized I loved working directly with our current customers so my managers helped me create an IDP plan to help me attain the goals I needed to in order to move into a customer-facing role. This plan helped me achieve my current role, which I love!

Employee Image
Faith, Customer Success Manager
Faith, Customer Success Manager

What People Are Saying About BigTime Software, Inc.

  • Strategic Vision & Planning: Public statements consistently outline an AI-first PSA growth strategy with concrete product priorities like intelligent workflows, predictive insights, and platform unification. Executive appointments and roadmaps connect leadership’s direction to identifiable initiatives across product and engineering.
  • Strong Execution: Release notes translate strategy into shipped capabilities such as AI-assisted expense management, invoicing improvements, a unified data layer, and a redesigned experience. The ongoing platform evolution indicates continual delivery against stated priorities.
  • Open & Transparent Communication: Company materials describe regular all-hands, an open-door approach with senior leadership, and formal mechanisms to gather input and communicate themes and action plans. These practices are positioned to keep a distributed workforce aligned on strategy and changes.

BigTime Software, Inc.'s Benefits

Hosts in-person all-hands meetings

We have a company wide meeting in Chicago once a month to ensure that all of our employees, across our different locations, are alligned on everything going on at BigTime

Hosts in-person revenue kickoff meetings

Implements team-based strategic planning

Open office floor plan to encourage communication and collaboration

Uses an OKR operational model to clearly define goals and priorities

Utilizes an open door policy that encourages accessibility