CTO VP of Engineering

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Larry Heminger, CTO

Q&A

*. Briefly describe the organization for which you currently or previously worked. What was the departmental structure (who do/did you report to, how many reported directly/indirectly to you, etc.)?

In summary, I have built and managed cross-functional engineering teams of varying sizes from as small as six to over 70. I have been in engineering leadership roles for over 20 years, with the most recent eight years in executive management positions as a key member of the executive team, across several vertical business sectors.

During my eight years at EcoATM, as VP of Technology I was part of the executive management team and reported direct to the CEO. Over the first four to five years, I grew the technology organization from only a handful of us post Series A funding, to going public through acquisition at which time I had a department of approximately 70 cross-functional engineers (both local and remote) organized into seven teams. I had seven direct reports consisting of Senior Directors, Directors and a Senior Manager of their respective teams. The department grew during this time frame both organically as well as through acquisition. For example, I took over a remote engineering team in Boston as part of the Gazelle.com acquisition. My teams consisted of software developers, QA/Test Engineers, Cloud & DevOps Engineers, Data Engineers, Business Intelligence (BI) developers, and agile project managers. I find it effective to organize my teams by value-stream, with each being responsible for either a product line or significant component of our overall enterprise system. I strive to have each team as independent as possible, reducing dependencies on other teams and external resources, yet strongly enable and encourage cross-functional and cross-team collaboration to optimize team flow as well as increase productivity of the department. I also maintained a cross-team matrix-style structure by skillset, including SW Development, QA and DevOps Engineering in order to develop and standardize best practices.

Each of the above teams also included several dotted line reports, such as product management, user experience, and business analysts. Both product management and business analytics team members formally reported to our CFO, but I was strongly in favor of having them work together on a day-to-day basis with the technology teams, as the most efficient product development approach. In each of my roles since ecoATM, including my most recent position as CTO for Automated Retail Technologies (ART), I have reported direct to the CEO and have been a member of the respective executive team. At ART, I was responsible for software and hardware development, product management and user experience (B2B and B2C). I had two teams, with my VP of Software, Senior Mechanical Engineer, and User Experience Designer as direct reports and a total department size of ten, in additional to several contractors, agencies and major supplier partners. At each of my companies, my teams have consisted of local, remote and off-shore resources. 2. Elaborate on your experience in the following areas: a. Client Communication/Development

For most of my professional career, I have been involved in regular communication with our clients, investors and other stakeholders in the form of client meetings, presentations, board meetings, product demonstrations, and pre-sales meetings. I am comfortable and confident meeting with my clients and stakeholders and I present a sense of passion and confidence when speaking. I enjoy Page 2 of 6

the opportunity to listen to the voice of the customer, and collect their feedback for continuous product improvement. I have received good feedback in the past that my vision and execution presentations are easy to understand by non-technical business executives. I pride myself in my ability to take complex technology concepts and translate into key business takeaways. Most recent examples include:

• Traveling to meet with our vending partner clients while CTO at Automated Retail Technologies (ART), to understand their software integration and business needs, and instill confidence in our solution.

• Also, as CTO at ART, I met with our primary investors during their due diligence to provide an overview of our product architecture as well as hands-on demonstrations of our product, which helped to successfully close our funding round.

• As CTO at Sapiens Data Science, I regularly met with potential clients and partners to demonstrate our B2C solution, as well as to discuss B2B integration opportunities and ways to enhance our partner’s offering by using and embedding our services into their platforms.

• As CIO at MemComputing, I routinely met with customers to scope out project details and any customization of our software that was required. b. Software Development

I am a professional computer engineer by degree, and have been emersed in the software development ecosystem my entire career. I started as a developer early in my career, and quickly discovered that I have a passion for the larger picture strategy and for managing teams of engineers. To this day, I am hands-on with system and software design and adept at architecting cloud-based solutions. I routinely work closely with my software teams to perform and facilitate design and code reviews. I no longer, however, consider myself a contributor to production-level code.

I have successfully designed and architected enterprise-scale software and SaaS products using various software technologies including .NET, C#, C++, Java, Python, Node.js and Ruby-on-Rails. I am also passionate when it comes to data engineering and business intelligence, having a strong skillset in both relational databases (RDB) as well as semi-structured (NoSQL) data. I have built several big data architectures and data lakes using technologies such as Snowflake and AWS Redshift, as well as business analytics platforms such as Tableau, Power BI, and AWS Quicksight. c. Process Development

I have often been charged with defining and documenting a software development lifecycle (SDLC) process for many of my companies, as far back as 2000 when I was Director of Engineering for AGFA Healthcare. My processes follow the Agile Methodology, and focus on breaking down large projects to streams of smaller units of work (a product roadmap), in order to deliver value and product features to the company frequently and predictably. I have developed many SDLC processes over my career, combined with leveraging industry best practices, published and validated approaches to keep my processes lean and flexible. I am also experienced and knowledgeable in defining development processes that fully satisfy data security, data privacy, change control, and information security compliance requirements. 3. How would you describe your project management skills? What is your methodology when charged with leading major projects?

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As I mentioned above, my project management style leans towards an Agile Methodology, where I break down larger efforts into a roadmap or stream of smaller milestones and objectives. I feel strongly that it is always better to deliver and demonstrate project functionality regularly and incrementally in smaller pieces, where we can validate our solution both internally as well as with our clients and stakeholders along the way. This approach also helps to reduce project risk and align business priorities.

In addition to an agile approach, my project management technique could also be referred to as

“peeling the onion”. What I mean by that, is I tend to emphasize creating the outer framework of the system or software first, enabling the team to implement and test end-to-end communications and integrations early in the project. This technique further reduces project risk, and gives the entire project team an idea of what it will look like when complete. The detailed implementation, user experience and business logic can then be added to the outer framework, usually more quickly and easily than doing it all at once.

My projects are always milestone driven with frequent checkpoints for alignment and validation across the organization. I find it is easier to gain accurate project status, reduce project risk and to respond to small pivots in the project plan or system design when we are completing smaller objectives on a regular basis. This approach also tends to gain trust and confidence with the project team as well as my executive leadership.

4. Describe your experience translating technology initiatives and communicating new ideas to your direct reports and/or senior management team. I am a big picture thinker, and I lean towards putting initiatives, goals and objectives into the larger context when communicating with my teams as well as my senior management peers. In my experience, I’ve discovered that if I can clearly communicate the “Why” we are doing certain things, and how those initiatives or new ideas fit into the bigger picture and context, then it’s easier for those individuals to understand and align to those initiatives. I also commonly leverage the Objective/Key Result (OKR) framework to ensure individual and team objectives are well-aligned with company and business initiatives, along with clearly defined metrics of success. As an engineer, I am effective in communicating technology priorities to my engineering teams and helping them understand how those priorities map into company objectives. From a senior leadership viewpoint, I am able to translate technology initiatives into improvements to key metrics and KPIs, thus demonstrating the business benefits. I also feel that it’s important to have frequent conversations with my direct reports, and not wait until there is a change or new initiative. It’s important to build that trust and relationship along the way, and to create a safe environment for collecting and discussing feedback on a regular basis. 5. Summarize your leadership style. How do you motivate and mentor staff? How do you handle training and keep staff abreast of current trends? I am an empathetic leader. Specifically, I strive to understand and put myself into the shoes of not only my direct reports and my teams, but my executive leadership team, clients, investors and stakeholder as well. My ability to understand, translate and map company goals and objectives into individual plans, projects and technology initiatives is one of my strongest skills. Page 4 of 6

My goal is to understand and identify with my direct reports and team members, to be vulnerable, and to establish a culture of open and honest communication. I strive to create an environment that is a win-win for both the company and team members. I’ve found that when my team members and direct reports feel valued for their contributions and opinions, that it creates a culture of engagement and is one of the most powerful motivational factors. For engineers specifically, it’s important to ensure their software gets utilized and deployed frequently. There is no more powerful motivational technique for engineers, than having the result of their hard work and efforts being utilized by our clients, to the benefit of the company. As CTO, one of my roles is to continuously ask questions and seek to understand potential ways we could do things differently in order to improve performance, reliability, quality, reduce cost or provide other benefits. When appropriate, I will assign a research task to my team members to look into alternative approaches either through self-learning, by attending a conference or technical session, and/or by developing a prototype to learn a new technique or technology. As an assigned task, I request a summary report and recommendation at the conclusion to help us decide whether we should take action and utilize the new technology or not. I find that a task-based assignment provides a better and more concrete learning experience for the team member, and results in a more actionable plan for the evolution of our technology architecture. 6. The information technology industry is ever evolving. What is your philosophy regarding staying up to date on the industry changes, certifications, publications, etc.? This is an insightful question, and one that I take seriously and proactively using several approaches:

First, I belong to relevant professional organizations such as 7CTOs. I’ve been a member of 7CTOs for nearly five years, and have found the organization an invaluable asset to me as a technology leader. 7CTOs provides an executive coaching framework specific to the CTO and senior technology leadership community. We are organized into forums of seven members each plus a facilitator who is a licensed professional coach. We meet in-person on a monthly basis, to process, discuss and support each other’s challenges, both technical and from a leadership and emotional intelligence (EQ) perspective. It is extremely helpful to me to understand the challenges facing my peers across numerous industry sectors, and to discuss and define standards of behavior to bring out the best performance in a CTO.

I was honored in 2020 to receive a San Diego Top Tech Award for my work while CIO at MemComputing. As a former award winner, I am now participating as a judge for the Top Tech Organization, and have an opportunity to interact with and learn from exceptional information technology leaders across a variety of businesses. I also belong to SIM San Diego, which is a non-profit professional organization inclusive of both Information Technology (CIO) and Product Development (CTO) leaders. This is another example of ways I’m able to exchange information with my peers in similar roles, to see what technologies they may be using to solve their challenges. SIM San Diego hosts regular round tables, technology summits and panels, which I attend when possible.

Second, I volunteer my time as a technology mentor to early stage and small businesses through non-profit organizations including Connect Springboard and Startup San Diego. By learning about the technology challenges facing literally hundreds of small companies, I can both help them think through their technology strategy as well as learn and keep current with the most recent technology trends. Through my volunteering efforts, I have realized that I’ve developed into a better engineer and CTO.

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Being a CTO means always learning, and understanding that the ever-changing nature of information technology is the norm, not the exception. 7. What would be your approach to immersing yourself in the culture of a new organization while working in a remote environment? I don’t view my approach to be vastly different between in-person and remote, albeit in the remote environment I need to be more proactive and purposeful about establishing relationships due to the lack of spontaneous interactions. My approach to learning a new culture, new company, and new product is two-fold: (1) Top Down and (2) Bottom Up, as follows: Top Down: This applies to my executive peers, senior management team, clients, investors and other stakeholders. My goal is to fully understand our business drivers, sales and marketing priorities, expectations, product requirements and timelines, and any existing pain points to be solved. The net result for me is to achieve alignment on what success looks like from the executive perspective, and understand WHY we are building what we’re building. I would proactively reach out to the executive and senior management team, establish personal relationships though regular video calls, and develop a set of priorities and metrics which we can use going forward to manage and report performance of the technology team.

Bottom Up: This applies to my direct reports and teams. The purpose of bottom-up is to establish ground truth and details on WHAT we are building, HOW we are building it, and learn WHO I have on the team building it. An important goal for me during this process is to establish personal relationships with my direct and indirect reports, by being both vulnerable and empathetic, using video, chat and other techniques as applicable, and to develop an in-depth understanding of the technology, architecture, design of our product, and its strengths and weaknesses. I would want to accomplish the above top-down and bottom-up objectives within the first 30 to 60 days in the role, and then begin a gap analysis between our executive level goals, objectives and expectations, and the bottoms up discovery of what, how and who we have. I would then use this gap analysis to propose any initial technology team initiatives to align with expectations. My belief is that having a plan for my first 30, 60, and 90 days in the role, will provide a catalyst for immersing myself and not only getting an understanding of the company culture, but also getting a deep understanding of the strengths and weaknesses of the product and technology team. Doing so remotely means I need to be more purposeful in planning and organizing these conversations, and really making an effort to get to know people personally, even via video meetings. 8. Looking back over the past several years, what strategic or tactical move would you have changed for your organization? Why?

While CTO for Sapiens Data Science, I took it for granted that we had achieved product-market-fit for our health and wellness data science application. I took the product positioning and go-to- market plan that had been established prior to my joining the company, and built a technology team, SaaS platform and mobile application to address the defined business model. As it turned out, the original business model and go-to-market plan was not fully representative of the actual client persona that would have bought our product. In retrospect, this experience taught me to ensure, and to challenge, when necessary, the assumed go-to-market plan, user requirements and end user persona in order to confirm we are targeting the product at the right user and payor. This experience also taught me the value of a simple and Page 6 of 6

inexpensive prototype which can be used to validate the go-to-market plan, but not be a significant investment so that we can easily pivot if necessary. 9. Describe your vision of the CTO role and how it will contribute to the future success of the company.

I strongly believe the role of the CTO is a business role, with the primary responsibility to align the technology platform, applications and engineering teams with the sales, revenue and other strategic objectives defined by the company, thus enabling the business to meet or exceed its success criteria. The role is critical to achieving company objectives through timely delivery of product features, high product quality, platform reliability, and best in class customer useability. I also see the role of the CTO as needing to protect and shield the business against competitors, especially in the areas of intellectual property and information security protection, and to ensure compliance with industry regulations and data privacy standards. I see the role of the CTO as an innovator, constantly looking for ways to not only improve existing capabilities by doing them faster, less expensive and/or with a better user experience, but also coming up with innovative new capabilities which set the company apart and clearly distinguish the company from their competitors.

Additionally, I see myself as an influencer. By establishing a trusting relationship with my executive peers and co-workers in other aspects of the business such as business development, sales, marketing and operations, and by asking intelligent questions, I’ve been able to have a positive impact on my previous companies outside my department as well. By listening to the voice of the customer, and continually learning and innovating with better ways to do things and developing new ideas to thrill and delight our clients, the CTO can enable massive success for the company.

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