Joshua Tillman and the business of dead air

Joshua Tillman wanted to spend less time waiting for the next conversation. At his internship, making hundreds of calls meant repeating the same small motions, with dead air scattered through the day. He was a UC Davis student studying economics and political science. He took the problem to engineering friends, who helped him build a prototype. A dreary assignment had acquired an interesting technical question.

“At first, I just wanted something to help me at my internships,” he later recalled. Six months after the prototype, he proposed starting a company. His friends were unconvinced. The dialer, however, had given him a reason to keep going. The idea that began at university in 2005 would become DialSource, then Conquer, a business built around the overlooked work that surrounds a customer conversation.

It is an appealing place for a software story to begin: the founder is also the person inconvenienced. There is no need to persuade him that the problem exists. He has another list of numbers to call.

An internship with too much waiting

Phone work makes repetition unusually easy to notice. A conversation may be different every time; the steps required to reach it are often painfully familiar. Dialing, waiting, finding the right information, and recording what happened can become a job wrapped around the job. Tillman’s early project took aim at that surrounding machinery.

The distinction between a promising student experiment and something a business can buy took time to work through. The project began in 2005. DialSource’s creation as a company followed in 2007. Its flagship CRM-native product arrived in 2009. Those dates describe different stages of the same undertaking: an idea, an organization, and a product ready to carry a larger ambition.

That sequence gives the story a useful sense of scale. Software companies are often compressed into their founding year, as though an incorporation and a working business were the same event. Tillman’s early years involved developing the answer. The later enterprise product would bring telephony, analytics, and automation together inside customer relationship management software.

The school colors came along

Tillman carried his university loyalties into customer meetings. At Stanford, he arrived with engineers dressed in UC Davis gear to demonstrate DialSource. The campus rivalry supplied its own entertainment: the visiting Aggies were there to explain the technology.

There was commercial confidence, too. He offered the Sacramento Kings business team dinner anywhere in the country, at his expense, if his product failed to set new quarterly records. A month later, the Kings signed a contract. It was a sales pitch with a restaurant bill attached.

The university connection went beyond a good story about shirts. Tillman’s attachment to Sacramento had practical foundations: nearby universities, technical talent, and a place where he wanted to build. He publicly praised the region’s access to capable people, its geography, and the ease of reaching other destinations. His case for the area joined recruiting considerations to the pleasures of living there.

That view makes his local pride more interesting than a slogan. A software company needs people who can work through difficult technical questions and stay with the product as it changes. A university relationship can keep introducing those people. Tillman treated his alma mater as part of the company’s continuing life, rather than a credential to be left behind.

“Sacramento Proud through and through”

Joshua Tillman, on his hometown connection

The work after the conversation

As DialSource developed, the scope widened beyond placing outbound calls. Automation and analytics became part of the proposition. Denali added support for inbound calls as well. The product was increasingly concerned with the information moving around a conversation: what a representative knew beforehand, what happened during the call, and which action should follow.

Post-call automation made that concern tangible. A completed call could trigger activities and updates inside the customer’s CRM. Different businesses wanted different data points and different sequences of actions. Tillman’s company worked on fitting the communications system to that environment, with Salesforce and Microsoft Dynamics as important homes for the product.

He also described an engineering approach that extended into the carrier network, software, and hardware supporting the service. A sales representative sees a calling interface. Behind that interface sit routing decisions, infrastructure, and the requirement that a conversation arrive intact. The apparently simple button carries quite a lot of company on its back.

The appeal of working inside the existing CRM was straightforward. Representatives could keep using a familiar workspace while calling and recording activity. Managers could inspect the results. For Tillman, the promise was that communications software could improve the work without requiring the customer’s team to organize its day around another disconnected system.

Tillman also credited the company’s relationship with Rackspace for giving his team access to technical expertise while freeing it to concentrate on development, deployment, and customers. He described being able to bring a technology question to the provider and have an expert appear. It is a less theatrical part of founding a software company than a sales wager, but an instructive one. A product that promises dependable communications needs dependable support behind it. The founder’s job includes deciding which capabilities to develop within the business and where a specialist partner can help the team spend its attention well.

A company learns to sell upmarket

Recognition accumulated as the product developed. DialSource appeared among the “30 Most Powerful Apps” at Dreamforce in 2013. Red Herring included it in its Global Top 100 in 2015. Denali received a Business Intelligence Group Product of the Year award in 2016. Tillman also received Sacramento Business Journal’s 40 Under 40 recognition that year.

The awards mark a period when the company was becoming more visible. Selling to large organizations brought another task: recruiting leaders who understood how those customers bought and deployed software. In March 2019, DialSource appointed former Hewlett Packard Enterprise executive Lars Fredrick Wold as senior vice president of sales.

The appointment explicitly supported a shift from smaller businesses toward enterprise customers. Wold had led HPE’s global inside sales and support organization, spanning more than 1,200 sales, support, and business development professionals across over 40 countries. That experience was relevant to a company trying to sell communications technology into larger, more complicated organizations.

Tillman described the hire as a way to accelerate enterprise growth and strengthen partner relationships. Omar Haq, identified then as DialSource’s co-founder and chief operating officer, also welcomed Wold. The student project now had a leadership team recruiting for a different scale of business. Building the product and building the organization around it had become parallel assignments.

In January 2020, Camden Partners announced it had led a $10 million round. The stated purpose was to accelerate growth and expand relationships with key partners. Camden partner Todd Sherman would join the board. Tillman spoke about helping teams work more efficiently as they engaged customers and prospects.

The financing belonged to a business already serving enterprise sales and service organizations. It put capital behind a direction the company had been developing for years. A larger round could support expansion; it also arrived with another experienced person at the boardroom table. The company’s circle of collaborators had grown considerably since the first conversation with engineering friends.

When the name caught up

By May 2021, Tillman was appearing at Startup Happy Hour as CEO of Conquer, the business formerly called DialSource. The new name accompanied a broader offering: voice, email, SMS, and social channels such as LinkedIn. A product associated with telephony had grown into a way of coordinating multiple kinds of customer interaction.

▶ WATCH THE CONVERSATION

His discussion ranged across origins, team building, culture, funding through sales, and adjusting to market demands. Those subjects fit the company’s progression. The practical concern was still how teams engaged customers, but the answer had expanded with the work. Rebranding gave the business a name with room for that expansion.

There is a pleasing mismatch between the modest scale of the original irritation and the range of work it eventually produced. A better way to get through calls led to questions about software architecture, enterprise selling, recruiting, and company identity. Each required people with different expertise. Tillman’s founder story contains repeated acts of bringing those people into the conversation.

The original problem travels

Tillman is Conquer’s founder and former CEO. By January 2026, the company identified Greg Moran as chief executive when it introduced Voice Plus, a mobile product for field sales teams. That later chapter belongs to the company under its subsequent leadership.

Yet the product’s stated purpose echoes the early concern. Field representatives need to make calls, record meetings, and capture notes while moving between appointments. Voice Plus was designed to put those activities into Salesforce with less effort. The setting had changed from a student’s internship to a representative’s day on the road. The awkward steps around a conversation were still worth someone’s attention.

That continuity gives Tillman’s career its shape. He started with work he wanted to make easier, found collaborators, and kept developing the answer as customers demanded more. For a business founded around the telephone, it is a fitting legacy: giving the conversation a better chance to happen, and giving what happened afterward somewhere useful to go.