Lindsay Frey once gave her sales team permission to stop impressing her with how many calls they made. She had been holding representatives to 80 to 100 call activities a day. Then she noticed the awkward question sitting beneath the numbers: what, exactly, had all that dialing achieved?
A rep could make 110 calls and have no worthwhile conversations. The spreadsheet would look industrious. The business would have little to show for it. In an account she first published in June 2012, Frey described telling the team at a morning meeting that she would stop watching call totals. She wanted meaningful conversations, qualified leads and pipeline. The new target was 15 meaningful conversations a day.
The result was pleasingly inconvenient for the old system. Call volumes barely changed, she recalled, but conversations improved. Reps gave each account more thought instead of trying to squeeze in a few final calls before going home. The telephone remained busy. It had simply lost its authority as a judge of character.
That early experiment offers a useful way into Frey’s working life. Today she is the co-founder and CEO of demandDrive, a Greater Boston sales, marketing and revenue operations agency. Its services have expanded considerably since 2011. Yet a question from its early years still fits: which part of the activity is helping someone make a sale?
“What type of management style do you respond best to?”
Lindsay Frey’s recurring interview question
An apprenticeship in the unglamorous part
Frey’s career runs through the machinery behind business-to-business selling. Her publicly listed work history includes client operations at AG Salesworks from 2002 to 2010, followed by an enterprise solutions sales management role at Percussion Software. She co-founded demandDrive in March 2011. She also lists a bachelor’s degree from Providence College.
Sales development representatives, usually abbreviated to SDRs, do the early work of finding potential customers, starting conversations and determining whether there is a worthwhile opportunity. Frey and fellow founder Dan Paul built a business supplying those teams and programs to B2B technology companies. It is work whose success depends on what happens before a polished presentation ever begins.
Training was part of the product. A demandDrive guide published in 2015 described a training program developed and refined by Frey over more than a decade in technology. Representatives had to demonstrate proficiency before becoming certified internally. Managers handled continuing training and call coaching, with weekly time devoted to improving performance.
That detail matters. Outsourcing a sales function means asking another business to trust your people with its first impression. Recruitment alone cannot carry the arrangement. A new rep needs to understand the account, judge a conversation and recognize when to ask another question. Frey’s early emphasis on preparation belongs to that very practical problem.
A cold call needs room for another person
Frey has also been on the receiving end of the sales techniques her company teaches. In a 2017 collection of SDR cautionary tales, demandDrive recounted her experience of callers who launched straight into an uninterrupted pitch. The performance could be so mechanical that she wondered whether she was listening to a recording.
Anyone who has answered an unfamiliar number can appreciate the predicament. A conversation has at least two participants; an information dump has a captive audience and an optimistic narrator. The story’s value is that Frey occupies both chairs. She runs a business that initiates calls, while knowing how those calls can feel to the person answering.
Her work with Lora Kratchounova of Scratch Marketing + Media widened the question beyond the phone. In April 2017, the two announced a joint report on account-based marketing, combining an industry survey with their experience supporting B2B clients. Their concern was how sales and marketing could work across the whole buying process.
The proposed route was deliberately manageable: try a focused account-based initiative alongside the existing approach, then evaluate it before a wholesale realignment. There is a family resemblance between that advice and the call-count experiment. Both make room to learn from a smaller change before declaring a new company religion.
The company gets a wider brief
By February 2022, demandDrive had approximately 175 employees. Everlane Equity Partners announced an investment in demandDrive and Data Fuel, the data business Frey had also co-founded. The transaction gave the founders a financial partner for the next stage of expansion.
Everlane described a recognizable customer problem: building an internal demand generation function takes investment, time and a willingness to tolerate turnover. demandDrive offered recruitment and development infrastructure that clients could use without constructing every part themselves. Frey credited clients, managers and team members for the first decade. Even after that work, she described the business as being near the beginning of its next phase.
The scope continued to widen. After the acquisition of Digital Impulse, the businesses adopted a combined demandDrive identity in September 2024. Digital marketing capabilities now sat beside the established sales services. Frey described her ambition as removing the barriers between departments that share responsibility for bringing in revenue.
There is an everyday organizational difficulty beneath that corporate language. Marketing may attract interest, sales may pursue it, and the technology between them must preserve the useful information. Each department can look competent in isolation while a potential customer disappears in the handoff. Taking responsibility for more of that journey changes what an agency is expected to fix.
The CEO who needed a use case
When her team began urging her to look at Clay, Frey’s response was hardly the enthusiasm of someone collecting software subscriptions. She wondered whether this was another AI tool to add. Noah Burkholz, who led revenue operations and go-to-market strategy, made the case through specific uses for the business.
Chief technology officer Peter Modest’s account gives the experiment a clear sequence. Burkholz began testing Clay in 2024. Automated research went into the manufacturing division in early 2025, followed by broader use during the year. The company upgraded to Clay Enterprise late in 2025. In January 2026, it reported millions of dollars in return on investment across the business.
In February, Frey joined Dan Paul, Modest, Burkholz and Tad Bustin for two days at Clay’s New York headquarters. Modest described whiteboards, coffee and discussions of what they could build together. The public partnership announcement followed in May. The sequence is useful: an internal experiment, working applications, a larger commitment, then an external offering.
In her conversation with Clay’s Nancy Mottice, Frey gave a concrete example. Research on large multifamily properties had taken an inside sales team three to five minutes per account. A workflow built by Burkholz reduced that task to about three seconds, she said. Those are reported results for a particular workflow, rather than a forecast for every sales team.
The small scale of the task makes it revealing. Finding information about a property is hardly the stuff of a cinematic technology launch. But repetition makes an ordinary delay expensive. Removing that delay leaves the rep with more time to use the information. The old question about the value of a busy day has acquired a new instrument.
A specific client example, shared in her 2026 fireside chat.
Nine appearances, and another change of method
Frey’s company reached No. 99 on the 2024 list of Massachusetts’ Top 100 Women-Led Businesses. That recognition puts her alongside leaders of businesses well beyond the sales technology circle. Her presence at the Boston Smart Business Dealmakers conference that year also placed her in the discussion about building and financing companies.
In August 2026, demandDrive announced its ninth consecutive appearance on the Inc. 5000. It reported a rank of 2,272 and three-year revenue growth of 148 percent. The ranking was its highest since 2018. Frey connected the company’s progress to an expanded focus on technology and processes alongside the people carrying out sales and marketing work.
Another milestone arrived on October 20, 2026: demandDrive announced that it had received Clay’s inaugural Rising Star partner award at the Sculpt conference in San Francisco. Clay’s partnership team pointed to the company’s experience using the platform internally before extending it to customers. For Frey, the stated opportunity was to connect fragmented data with practical sales execution.
Awards provide dates and milestones. The more interesting continuity lies in the decisions between them. In 2012, she changed what her reps were asked to count. In 2017, she and a marketing partner advocated testing a focused program. By 2026, the company’s technology work had moved from experiments into managed customer programs. Each step made the unit of improvement larger.
2018-2026 · No. 2,272 in 2026
148% three-year revenue growth, reported by demandDrive
Leave some judgment in the room
Frey’s advice on AI is grounded in choosing the problem first. She recommends identifying the organization’s three main challenges and building uses around those. Buying tools before knowing what they should accomplish risks leaving expensive capabilities idle. A software subscription, unfortunately, does not become useful merely because its renewal is automatic.
What excites her about the next stage is the ability of people without technical backgrounds to build useful workflows. That aspiration fits the training emphasis of demandDrive’s earlier years: give someone a clearer way to do the work, then let them develop the ability to do it well.
The connection across those years is an interpretation of her public decisions, rather than a claim that every move followed a master plan. Companies change, customers ask different questions, and a founder has to respond. Frey’s record is interesting because it contains visible revisions: to a metric, to a service offering, and to her initial skepticism about a tool.
There is something quietly demanding about her original sales experiment. Giving up an easy number means accepting a harder assessment. A meaningful conversation requires judgment. A qualified opportunity requires understanding. Fifteen years into demandDrive, Frey is still building around that harder assessment. The dial can count the calls. Somebody has to decide whether they were worth making.