TL;DR: Wendy Dole, Director of Engineering at Direct Supply, explains how senior living is being reshaped by workforce shortages, food costs, regulatory complexity, and the “silver tsunami” of aging baby boomers. She says engineering teams need to lean into AI despite legacy systems and uncertainty, improve how they work one bottleneck at a time, and keep both data quality and security top of mind. Her advice is to move forward with AI while helping engineers navigate the very real human impact of that change.
In this episode of Software Leaders Uncensored, Steve Taplin speaks with Wendy Dole, Director of Engineering at Direct Supply. Wendy describes Direct Supply as a company in the senior living industry that began about 40 years ago in the furnishings and equipment space and has evolved into what she calls an applied AI company.
What Direct Supply does
Wendy explains that Direct Supply originally focused on supplying furnishings and equipment to senior living providers, then recognized it could do more by applying technology to solve problems instead of only supplying products. She says that over the last 40 years, the company has continued evolving in that direction, with especially significant changes in recent years due to AI.
Industry pressures shaping the work
Wendy says the senior living industry is dealing with several major challenges, including:
- Workforce shortages
- Cost pressures
- Regulatory complexity
She explains that Direct Supply advocates for its customers through work in Washington and tries to help leaders understand the challenges facing the industry. She says labor is one of the largest issues and that the company is working on several products aimed at helping customers address it.
One example she gives is DS Smart, which helps gather vitals and record them into EMR systems. She also says Direct Supply is leveraging robotics and continuing to expand in that area.
On the cost side, Wendy notes that one of the biggest expenses in senior living beyond labor is food. She says Direct Supply has a line of business in spend management and launched a product called DS Menu last year to help with that challenge.
She also says the company has building management systems, which connect to regulatory challenges, and that there are many opportunities still ahead.
The “silver tsunami”
Wendy says one of the major demographic realities affecting the industry is that 10,000 seniors turn 80 every day, and that this will continue for another 15 years. She says 83 is roughly the age when people move into senior living. She describes this trend as the “silver tsunami.”
She says the result will be a severe lack of housing because there are not enough beds and rooms for all of the seniors who may need care. She also notes that higher census counts help providers financially because more filled beds can improve economics, but that those benefits bring the related challenge of having enough labor to care for more residents.
How Wendy got the role
Wendy says she has been with Direct Supply for almost four years. She explains that the Milwaukee technology ecosystem is relatively small, so many people know each other, and that Direct Supply reached out to her.
She also says one of the reasons she was able to land the role was her balance of technical skills and leadership development. Wendy describes having worked with a CEO at a previous company who helped her develop her leadership skills over several years. She says that while technology is easier to learn, leadership competencies are more difficult, and that Direct Supply was looking to bring in someone who could expand the leadership capabilities of engineering teams beyond technical skills alone.
Work model
Wendy says Direct Supply is hybrid, though it also has quite a few remote employees. She notes that during COVID the company hired more remote people, and that there is also an office in North Carolina with some engineering staff. She says that, at least in her area, almost no team is entirely located in one place full time.
Women in engineering
Wendy reflects on her experience as a woman in engineering, noting that when she was in college there were only two women in her major. She says she initially did not notice the imbalance as much because she was frequently in male-dominated settings, including serving as an RA on a men’s floor.
Later, when she worked in healthcare, she says there were more women in the broader technology department, especially in roles like BA, product manager, and systems analyst, even if not necessarily in engineering.
She says it was not until later in her career, while hiring, that she noticed how few female candidates were applying. She says she heard from younger people going through school that there were still only two or three women in the major, and that this made her reflect on how little had changed.
Wendy says she does not believe the Milwaukee technology environment is toxic in the same way Silicon Valley is often described, but she does see that the industry is still male-dominated. She emphasizes making women feel comfortable in engineering, building up other women, and moving away from the idea that there is only room for one or two women in the space.
Digital transformation gaps in senior living
When asked about digital transformation gaps, Wendy says one major challenge is that the industry often does not have much money to spend on technology. Because of that, she says Direct Supply has to show customers that buying their products will actually save them money or time.
She highlights two examples:
- Housekeeping tools, which help schedule housekeepers, determine when rooms are emptying, assign cleaners, and track when work is complete
- DS Menu, which helps facilities manage menus and dietary complexity while also responding to food cost fluctuations, such as egg shortages
She says these products are examples of where technology can reduce labor pressure and food costs while also improving operations.
AI hype versus reality
Wendy says the company has to lean into AI, even if some of the hype around it may be overstated. She focuses particularly on how much time AI can save engineers.
She says one of the biggest problems for her teams is that they are working with legacy systems, including some code that is 20 to 25 years old, and even some VB6. She says the challenge is figuring out how to harness AI to create new products while still working inside those old, interconnected systems.
Wendy says she believes teams cannot keep using legacy systems as an excuse for not moving forward. Instead, they have to lean in, solve one problem, then solve the next one, even if that means creating a new bottleneck each time. She gives examples like making engineers faster, then creating a code review bottleneck, then creating a testing bottleneck.
Her view is that even if teams only improve by 10 percent, that is still worthwhile.
Technical debt and modernization
Wendy says she has changed her own thinking over time about whether companies should build new systems, buy replacements, or continue investing in legacy systems.
She says in the past, it seemed more obvious that companies should replace older systems entirely, but that with AI helping accelerate development, there may be more middle-ground options. She says her current thinking is that AI can help make technical debt work take much less time, which changes the equation.
She says her team is currently at the point where they finally have systems that can index and inspect their repositories intelligently enough to ask better questions and get better answers about the code.
Backlog health and product pressure
Wendy says one challenge is that as engineering teams move faster, the rest of the organization has to keep up. She says this means product managers also have to move faster, make better decisions faster, and help teams absorb the speed that AI enables.
She says Direct Supply’s executives are bought into the idea that the company must work differently and move faster. The challenge now is helping product managers adapt and then helping users adopt the resulting changes.
AI will change engineering work
Wendy says she does not believe engineers will become obsolete anytime soon, but she does think their work will change significantly. She says engineers will need to operate more at a systems thinking level, coordinating AI and setting guardrails on what it can and cannot do.
She says this likely means less time typing code manually, more time coordinating systems, and more responsibility for setting thresholds, oversight, and controls.
She adds that she does not know exactly when that shift will become dominant, but believes it is already starting.
Talent and healthcare technology
When asked about the biggest engineering challenges in healthcare-adjacent industries, Wendy highlights talent constraints, the need to find engineers willing to lean into AI-native ways of working, the challenge of balancing rapid change while still delivering features, and engineers’ own fears about becoming obsolete.
She says the right response is not to resist change, but to lean into it and treat it as a productive source of pressure.
Data and data governance
Wendy agrees that data quality and governance are essential to making AI useful. She notes that while Direct Supply is mostly in the business side of senior living rather than direct patient care, some patient-related data is still involved.
She says Direct Supply has teams focused on ensuring the right data products are available, at the right fidelity, with appropriate access controls and guardrails. She says the company has been working on this for about three years and sees it as critical because AI cannot provide useful results without good data.
Security concerns
Wendy says she does not envy security teams, because she believes the industry has not yet seen the full extent of how AI will be used against companies by bad actors. She says organizations are trying to move very quickly while security teams are trying to protect them, and that finding the middle ground is difficult.
Looking ahead
When asked what might fundamentally change in the next three to five years, Wendy points back to the shortage of senior housing and the need to support more people who may have to remain in their homes longer.
She says she is interested in how robotics might eventually help solve that problem, even if today it still feels far away. She says that while the cost and capability of robots are not yet there, the need is real and something will have to change.
Advice to another engineering leader
If advising another engineering leader in a similarly regulated and complex industry, Wendy says the priority should be to lean into changing how teams work and leverage AI in every possible way. She says organizations cannot afford to let someone else figure it out first.
Final advice
Wendy’s closing advice is to lean into the changes AI is bringing, while also making sure leaders understand the human side of what engineers are feeling. She says those emotions are real and leaders need to help their teams through that journey.
