Our Firm



Director of Learning & Development


CentralSquare Technologies | General & Administrative | Lake Mary, FL

About CentralSquare Technologies

CentralSquare is a unique enterprise software company whose mission is to build safer and smarter communities.  The company serves over 7,500 organizations in North America, from large cities to counties and towns of every size.  They provide software for managing public safety (#1 market share) and public administration (#2 market share).  The company employs over 2,000 individuals in multiple North American locations.  More information is available at www.CentralSquare.com.


Its technology platform for public safety includes 911 call management, computer-aided dispatch, records management, mobile, citations, evidence management, and corrections. In essence, the company’s software empowers first responders to do their jobs as effectively as possible. CentralSquare has the opportunity to help first responders save more lives.  Based on recent studies, for every second the company’s ever improving software can shave off response time, one thousand lives are saved.


For public administration agencies, CentralSquare provides software for finance, human capital management, payroll, utility billing, citizen engagement, asset management, regulatory compliance, and community development. For government owned hospitals and clinics, it provides patient information, compliance, and analytics software. CentralSquare’s broad, unified and smart software suite serves 3 in 4 citizens across North America. With the efficiencies of Central Square software tools, administrators can spend more time on the big issues (education, homelessness, healthy patient outcomes, etc.) and less on fighting bureaucratic fires. Working at CentralSquare provides the opportunity to help improve the experience all of us as citizens have in interacting with our local governments. 


Central Square has the backing of two of the most successful private equity firms: Vista Equity Partners and Bain Capital.  The company was formed by these investors in late 2018 by the merger of Superion, TriTech along with Zuercher, and the public sector and healthcare business of Aptean. 


Both of these firms are committed to providing the support necessary to maintain Central Square’s outstanding growth trajectory.  The company has significant growth plans driven by continued product innovation, customer and market expansion and the shift from on-premise licensed software to a more cloud-based SaaS model. 

HR Purpose and Business Model Context

This is a highly visible leadership role that reports directly to the Chief Human Resources Officer (CHRO) and is based in the company’s Lake Mary, Florida headquarters.


”First we are a part of the broader team, in it together to win it…


Second we are HR professionals.  We contribute people, organization and culture solutions that are focused on enabling employees and teams to succeed and perform well…


 When employees and teams feel great and perform well, they deliver products and services that our customers love…


When our customers love what we deliver, they keep buying more – and the team wins – and the flywheel is complete.”

The context for the mission for this leader begins with the Purpose of the HR group within the larger CentralSquare purpose and mission:

HOW the HR group DELIVERS on this Purpose is the Business of HR, and the business model has three primary pillars:

Product Development

Professional Services

Customer Service

From idea to ready for “market” – design & develop products that will be used in the organization. 

Manage and improve these products through their lifecycle

        Recruiting & selection tools

        Training programs

        Incentive plans


        Engagement measurement


Help “clients” implement products in a way that translates into desired performance result.


Translate business plans into talent and organization plans that are integral to success.  Drive achievement of plans and change.  Iterate in product development as needed

As employees go through their life at the company, they will need help with HR products and services: 

        Discovery of support available for life events

        People managers seeking tools and clarity

        Learn or solve issues with an HR technology tool

        Manual transactions

        Exception and error handling


These require similar processes and tools and personal support to what many great companies provide to their customers






Mission for the Director of Learning & Development

The over-arching mission of the Director of Learning & Development (L&D) is to plan, build and implement learning solutions to that enable CentralSquare’s employees to achieve and surpass their performance and personal development goals. As an enterprise leader and owner of this corporate function, the Director of L&D plays a key role as a champion of the company’s core value of “Growth Mindset” that is integral to the company’s mission and growth strategies. While much progress has been made on this mission since the merger of four small companies one year ago, many of the required learning solutions and capabilities are nascent or require a fresh start.
Skills & Requirements

Scope of Responsibilities

The Director of L&D is responsible for design, development and implementation of solutions in the following areas:

·       New hire orientation/onboarding – with a focus not just on day 1 – but also on goals for speed to proficiency for entry-level in roles such as software engineering, professional services and customer support

·       Performance management process (in partnership with Director of Compensation as part of a pay for performance philosophy) with a focus on employees receiving coaching for success throughout the performance cycle

·       Targeted development of the people manager population to continually improve their ability to perform their management responsibilities.  The Director will personally assist with senior leadership development efforts. 

·       Providing a platform and process for ongoing skill development for employees, in service of both the mastery of their current job and their long-term personal development goals

·       Supporting large change initiatives in the company through training that is integral to the change management plan. 


The Director leads a small team of learning and development specialists and manages vendors in order to design, develop and deploy these solutions.  This is a hands-on role where the Director is both a “player and a coach”. 


To develop effective learning solutions in these areas, the Director of L&D leverages a variety of tools and approaches including, but not limited to: instructional design, blended learning delivery methods, competency gap analysis, defining scope of work, a defined training design methodology, process improvement, change management, coaching, evaluating learning impacts, and performance improvement.


The Director of L&D plays a central role in reinventing learning models, learning systems, delivery methods and external vendor partnerships, as well as creating in-house programs, as needed. The use of more blended, virtual, self-directed and experiential learning models is emphasized over traditional classroom delivery, so adaptability, creativity and sustainability are important. Demonstrating strong curiosity and a high degree of capability with gathering and organizing the data involved in learning programs is critical, as the responsibilities involve continuous inspection for effectiveness and identification of opportunities to simplify and scale.

Experience / Expertise Required


·       Bachelor's degree required, Master’s preferred in a training and development or organizational development related field. Degrees might include Knowledge Management, Organizational Development or Organizational Psychology, Human Capital Development, Technology Education or Instructional Design.

·       10+ years of progressive and successful experience in learning & development, organizational development, leadership development and/or leading organizational change. Demonstrated expertise in the portfolio of methodologies described in prior section and utilizing those methods to design and implement effective learning solutions. 

·       Possesses an innate understanding of the mindset and high-speed cadence of a high growth software development company.  Ideally has extensive experience in enterprise software companies (but not required).   

·       At least 5 years of direct people management experience – ideally more extensive people management experience to inform solution design with practical perspective.  Proven ability to focus, motivate and develop people.


Personal Skills and Attributes Requires


·       Proven business acumen (understands how a company makes money, can articulate company goals & business objectives, understands the customer segments served by the company and the key products & services).  Bases solution design in business context. 

·       Strong consulting, stakeholder management, and presentation skills with demonstrated ability to influence senior leaders.

·       Role models trustworthiness in behaviors and actions

·       Strategic thinker balanced with ability to roll-up the sleeves and personally do whatever it takes

·       Makes decisions & recommendations based on data and facts.  Demonstrated ability to use good measurement systems. 

·       Demonstrated strong facilitation skills large & small groups, asking powerful questions and encouraging candid discussion to help deepen and solidify learning.

·       Highly flexible and self-directed with the ability to work under tight deadlines and manage multiple and shifting priorities in a fast-paced environment. Comfortable with rapid iterative approach to building and improving.