There are markets so enormous that a marketer can lose herself in abundance. Then there is the market Kelly McDermott faced at Caregility: a few hundred large health systems, each containing a maze of hospitals, committees, clinical leaders, technologists, budget holders, and people sensibly worried about making an expensive mistake. It was not a haystack in need of more hay. It was a room with roughly 300 doors. Her task was to learn which 60 might be opening.
This is the quiet drama behind McDermott’s work as Caregility’s Chief Marketing & Customer Success Officer. Caregility builds the video, communications, and connected-device infrastructure used for virtual nursing, observation, and other hospital workflows. Buying it is not an impulse. McDermott has described sales involving upward of 15 stakeholders and lasting seven to 18 months or longer. A conventional torrent of leads would create activity, then paperwork, then the melancholy discovery that activity and progress are distant cousins.
So she helped replace volume with attention. The company narrowed its view to about 300 enterprise accounts, watched for signs of genuine research, and coordinated marketing, sales development, sales, and eventually customer success around what each account appeared to need. The method has an unglamorous virtue: it accepts reality. At any given moment, McDermott estimated, only about one fifth of those accounts were actively looking for a solution. The other four fifths did not require a louder advertisement. They required patience.
The comedy writer in the control room
McDermott’s professional biography reads like a tour of the systems that taught modern offices to talk: voice, video, data communications, software, security, cloud computing, and integration. She worked at Wire One Technologies, founded Zephyr Strategy, led marketing at TriNET Systems and Carousel Industries, became a founding partner at Department 60, and moved through Layer Logic and Yorktel before joining Caregility in 2019. Along the way she earned an MBA from Longwood University and served as president of Women in Technology in 2011-2012.
There is a second line on the résumé, and it makes the first more interesting. In 2013 she published Did I Say That Out Loud?: Conversations About Life, a 122-page collection of comic personal stories. The title came from a plaque given to her by a friend. Her author’s note declares that the events are 87 percent true and cheerfully charges the remaining 13 percent to her Irish heritage. The table of contents moves from “Coupon Queen” to “My Cat’s Butt” to “What I Would Say If I Were the Flight Attendant.” It is not standard preparation for enterprise revenue strategy. Then again, standard preparation rarely teaches a person to notice what everyone else is trying to pretend did not happen.
“Marketing is more than selling - it’s about storytelling, teaching, and inspiring.”Kelly McDermott, on her LinkedIn profile
The humorist and the operator share an instrument: close observation. One watches a conversation go sideways at dinner and knows where the story is. The other sees an anonymous rise in web traffic from a hospital network and knows not to pounce. McDermott’s marketing philosophy begins with story, but her account-based work insists that the listener earn the right to tell it.
A sale drawn as a journey, not a funnel
Her most revealing case study begins in January 2022, when Caregility noticed increased website traffic from a major hospital system. The account was researching. For roughly three months, the team allowed that curiosity to develop while directing awareness advertising toward matching traffic. In April, after contacts identified themselves through forms, an SDR began conversations. More people downloaded material, joined webinars, and took meetings. In July, Caregility was invited to present to 30 decision-makers and influencers. The map grew crowded. The deal closed in the first quarter of 2023, more than 13 months after the first signal, with the hospital system buying two solutions.
The sequence explains why McDermott brought sales development into the marketing organization. SDRs could work beside marketers and account executives, identify the actual buying group, and turn faint digital signals into useful human conversations. She called them a “farm team” for future sales account managers. The phrase is generous and exact. Their job was not merely to feed meetings into a calendar. It was to learn the market well enough to grow into the next job.
It also reveals McDermott’s preference for joint ownership. Linear handoffs work beautifully in diagrams and rather less beautifully among human beings. Her model asked marketing to create relevant material at scale, SDRs to discover and nurture stakeholders, sales executives to develop the commercial relationship, and all of them to work from a shared account picture. The customer did not experience four departments. The customer experienced one company that either remembered the conversation or did not.
The single source of truth has several tabs
Caregility’s stack brought together Salesforce, Demandbase, Pardot, website analytics, LinkedIn and Google advertising, trade-show scans, form fills, webinar registrations, business cards, and sales notes. McDermott wanted a unified view of each account. What she got, as most honest operators do, was a useful view with seams.
“Despite the relative sophistication of our marketing tech stack, we’re still dealing with data silos and a reluctant reliance on Excel.”Kelly McDermott, writing about complex B2B sales
That sentence deserves a small brass plaque of its own. It removes the showroom lighting from marketing technology. Salesforce could remain the official record while missing touchpoints. Sales representatives could learn something valuable and neglect to put it into the CRM. Separate platforms could each preserve a different truth. Attribution, the dream of assigning every dollar its proper parent, still involved meticulous manual work.
McDermott’s response was neither despair nor another miracle purchase. The team assigned a full-time demand-generation specialist to own the ABM platform and process. They configured intent terms for their particular market. They connected systems, endured false starts, and treated adoption as organizational work. Her recurring point in interviews is that the technology is the smaller piece. People and process decide whether the information becomes action.
Tools can reveal that an account is moving. Ownership determines whether anyone responds. McDermott’s ABM program matured when one person had the time and mandate to run it, while marketing, SDRs, and sales shared the account map.
The ampersand in her title
McDermott is now Chief Marketing and Customer Success Officer. The pairing looks unusual only if a company imagines that the story ends at purchase. Her ABM work was already moving in the other direction: from winning new logos toward “land and expand,” with customer success participating in a total customer-growth team. Marketing could help identify the right account and set an honest expectation. Customer success would learn whether the promise survived contact with daily work.
In August 2026, that responsibility appeared in a prosaic and telling announcement. Caregility added DataSource Technology to its service ecosystem for preventive maintenance. Some Caregility devices had been in production for more than eight years, McDermott said. As fleets grew, keeping them ready required more proactive attention. The company reported more than 30,000 connected devices, over ten million virtual-care sessions each year, and 99.98 percent platform availability. At that scale, customer success is not a festive email. It is a device working when somebody needs it.
Her public comments on Caregility’s direction extend the same logic. Virtual care, she has written, should sit inside the care journey rather than remain an optional extra. Responsible AI, secure communications, and real-time information should appear where the work happens. This is not marketing as decorative language applied after engineering. It is marketing as the discipline of explaining what the product must reliably do, then staying for the consequences.
A career built around the useful signal
McDermott’s range can look eclectic: executive, strategist, founder, nonprofit president, arts board member, humor author. Look again and the connective tissue becomes obvious. She has spent a career studying communication systems, including the oldest and least predictable one, the person at the other end.
The account-based program gave that instinct an architecture. Limit the field. Learn who is genuinely moving. Do not confuse anonymity with disinterest or a form fill with commitment. Gather the people who each hold a piece of the truth. Keep listening after the contract is signed. Admit when the elegant platform still needs a spreadsheet. Laugh when appropriate, which is more often than the quarterly plan suggests.
In a business culture fond of acceleration, McDermott’s most useful idea may be tempo. The Caregility team waited three months before approaching the hospital account, then worked it for another ten. Nothing about that was passive. The quiet period created information; the busy period created trust. By the time two solutions were purchased, the marketing story had become a collective operating history.
Three hundred doors. Sixty with a light visible underneath. Fifteen people behind one of them, each carrying a different question. McDermott’s work is to know which knock will sound like help rather than noise. The comic writer understands the danger of speaking too soon. The executive has built a system for getting the timing right.