How ConnectWise company culture sets up our people for success

| By:
Jen Locklear

A recent Forbes article stated that 2022 is the year of workplace culture, and we agree. The general culture shifts happening with the Great Resignation and the Great Reshuffle clearly indicate that company cultures must shift too.

At ConnectWise, we know that great culture doesn't "just happen," so we have spent many years creating a thoughtful, flexible culture that can support our diverse colleague landscape, including a monthly survey to capture feedback. We care about the lives of our colleagues and want them to have the freedom to be present in their lives, so they can come to work focused and happy.

Here's how we strive to create a positive, inclusive work culture that includes the flexibility and freedom colleagues need to keep taking care of business in their work and personal lives.

ConnectWise Culture

Our emphasis on a positive and welcoming company culture, including an innovation-first mindset, has encouraged our colleagues to vote ConnectWise as one of Tampa Bay Time's top workplaces for ten years and counting! We focus on many essentials to ensure our culture keeps improving and changing as the workforce changes.

Our core values

Our core values apply to everything we do at ConnectWise, including our culture. As our colleagues internalize these values, it becomes a natural way to build a culture of mutual trust, respect, and accountability.

We live and breathe our core values, which gives us a distinct advantage. Our core values serve as behavioral and decision-making guidelines for the entire company, empowering every colleague to share ideas and make daily decisions that support their teams, our partners, and the ConnectWise mission and vision. Our six core values are:

  1. Drive partner success
  2. Innovate everywhere
  3. Make a difference
  4. Perform as a team
  5. Take pride in our work
  6. Own the outcome

As an extension of our core values, we have several guiding principles that serve as a compass for making decisions that align with company goals.

Emphasis on diversity, equity, and inclusion

We established a diversity, equity, and inclusion (DEI) council to help take actionable steps and pursue DEI initiatives that ensure we are measuring the effectiveness of our efforts and making adjustments as needed. 

The DEI Council works closely with our Executive Leadership Team on the following initiatives to make ConnectWise a more diverse, equitable, and inclusive place to work and belong. 

  • Diversity training: Our leadership teams received DEI training facilitated by a third party in Q1 and Q2 of 2022. In addition, we're working with the ConnectWise Talent team to coordinate interview-based hiring training designed to focus on awareness and perspective around DEI inclusion topics. Our goal is to reach every colleague with DEI training by Q3 2022.
  • Attract, recruit, and retain diverse talent: We actively recruit on alternative job boards with DEI-friendly and inclusive keywords. We also have goals to streamline and standardize ConnectWise job descriptions and job postings. In July 2022, we will move to a new applicant tracking system that provides an interview scorecard to our hiring managers, helping remove unconscious judgments and further enabling a fair evaluation of candidates' aptitudes and skillsets.
  • Career advancement and equitable opportunities: We are collaborating with Mercer, a global professional services company, to create a job architecture and career framework designed to map and streamline jobs across the organization. Our goals include outlining skills and competencies that colleagues need to grow in their position. In addition, we identified career paths for all ConnectWise roles in India.
  • Job architecture and career framework: The job architecture and career framework project will create a blueprint of job families and map each colleague to the appropriate role. This final stage also encompasses assigning salary bands to job families and roles to give colleagues insight into different career levels and career paths at ConnectWise.

Colleague recognition programs

We incorporate a cheers system that allows colleagues to shout out others for a job well done, and we offer incentives to those who go above and beyond.

  • Passport to Success
    We offer a yearly trip to a select few colleagues as an incentive for embracing teamwork, innovation, coachability, and client delight. Our chosen colleagues (and a plus one) went to Curaçao this year, and next year's awardees will head to Hawaii!
  • Peer Recognition Program: The Hoot
    When it's time to send some kudos, we encourage all colleagues to send "Woo-Hoots"! You can turn your points into eGift cards, ConnectWise swag, or charitable contributions.
  • Dedicated Decade Trip
    We are truly grateful to colleagues who grow their careers with us. Our Dedicated Decade program includes a 10-year work-anniversary trip each year to express our appreciation. This year colleagues (and a plus one) enjoyed their stay on a beach in Sarasota, Florida. One colleague even got engaged on the trip!

Colleague health and wellness

  • Embracing hybrid work
    We've recently relocated to a new office location in downtown Tampa, but many of our colleagues continue to enjoy the flexibility of working from anywhere. We also schedule virtual and in-person team bonding events.
  • Ginger: Mental Health Advocate
    Ginger is a confidential, on-demand coaching, teletherapy, telepsychiatry, and guided self-care program. Seconds after downloading the Ginger Emotional Support app, colleagues can access health coaching 24/7/365.
  • Volunteer opportunities
    ConnectWise colleagues have plenty of opportunities for philanthropic work, such as joining in hurricane relief efforts, working with the Computer Mentors' Teen Business Challenge, raising funds for Success 4 Kids & Families, and volunteering at the Orlando Day Center Nursery. We've also recently added two days of paid time off for volunteer work.
  • Meeting etiquette
    Our policy includes no meetings that could be an email and no meetings over the lunch hour or late Friday afternoons so that people can wrap up the work week before the weekend. Meetings are either 25 or 50 minutes to ensure breaks.
  • Wellness Committee
    This internal committee provides opportunities and activities to promote physical and emotional health. Events are held both in-person and virtually to serve colleagues worldwide. Recent events include the formation of a kickball league and a walking steps competition.

Career development

  • Tuition reimbursement
    Any colleague with one year of service at ConnectWise are eligible to apply for our Masters Assistance Program (MAP). We want to invest in our greatest asset, our colleagues. That's why we offer financial assistance when colleagues seek advanced degrees that will further their careers. It supports our corporate social responsibility initiative of investing in a brighter tomorrow through developing our colleagues into top-tier leaders and innovators.
  • Internal leadership training
    "Leaders are made, they are not born. They are made by hard effort, which is the price which all of us must pay to achieve any goal that is worthwhile." We believe in what legendary football coach Vince Lombardi said. That's why we offer several career development training sessions, including how to have crucial conversations and navigate transitioning to a management position.
  • Career development program
    Career development is important to many colleagues and helps them feel fulfilled and happy at work. We provide a framework for colleagues to take the initiative and develop their own career plans with the support and guidance of their managers.


At ConnectWise, we see it as our responsibility to give our colleagues access to the tools, training, and collaborative company culture they need to succeed at work and in life. As the world and colleague needs change, we are prepared to listen, learn, and stay flexible to ensure we fiercely protect a company culture that supports our company's and colleagues' needs.