How Regiment Securities Transformed Sales Operations While Maintaining FINRA Compliance
From Manual Prospecting to AI-Powered Lead Generation with Human-Touch Conversion.
The Big Picture
In the world of financial services, innovation often collides with compliance requirements. For Michael Cavanaugh, Chairman and Registered Representative at Regiment Securities, this tension was the primary constraint limiting his firm's growth.
The “traditional approach” wasn't working. Cavanaugh found himself personally making hundreds of cold calls to generate five meaningful conversations per day. "I don't have the time and energy to make 100 phone calls in a day, while I'm doing all this other stuff," Cavanaugh explains. "The biggest challenge in our industry is to have the people to actually make the calls."
Regulations made the problem even more complex. Many sales automation tools that worked for other industries created dangerous "gray areas" for Registered Representatives under FINRA oversight. Meanwhile, digital marketing costs were rising, qualified sales talent was difficult to find, and competitors were finding ways to gain efficiency advantages.
The breakthrough came through an unlikely combination: an inbound AI system called "Mo Money" integrated with Tendril's agent-assisted dialing solution. This partnership would deliver what Cavanaugh describes as "improved operational efficiency and scalability while maintaining procedures aligned with FINRA compliance standards”.
About Regiment Securities
Regiment Securities is a FINRA-registered broker-dealer founded in 2021 and based in Chicago. The firm operates as a placement agent and financial advisor with a specific focus on markets that traditional investment banks often overlook or underserve.
Core Business Focus:
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Capital Raising & Advisory – Structuring debt, equity, recapitalizations, and liquidity events for lower and middle-market companies.
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Alternative Asset Placement – Acting as placement agent for private equity, venture capital, credit funds, and digital asset opportunities.
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Family Office & Founder Advisory – Helping founder-led businesses and family offices structure financing and build investor relationships.
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Ecosystem Approach – Combining traditional investment banking expertise with modern, tech-enabled processes.
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The Challenge: Regulatory Constraints & Scalability
As a FINRA-registered broker-dealer, Regiment Securities operated under strict regulations governing Registered Representatives' communications. Any technology implementation had to navigate what Cavanaugh describes as the "gray area" of AI automation in financial services outbound communications.
The Operational Reality:
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Daily Target: 5 meaningful conversations per day represented the goal and ceiling of manual effort.
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Time Constraints: 100% of Chairman's time consumed by prospecting instead of high-value activities.
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Monthly Capacity: Maximum of ≈100 meaningful conversations per month at peak personal capacity.
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Scalability: Growth fundamentally limited by human capacity and regulatory constraints.
The math was brutal. Even working at maximum capacity, the firm could generate only about 100 meaningful prospect conversations per month. This created an insurmountable bottleneck: the firm's growth was capped by Cavanaugh's time to make calls, not by market demand or capital availability.
Traditional solutions weren't viable. Hiring more sales staff meant extensive training, compliance oversight, and no guarantee of success. Fully automated AI calling systems created regulatory risks that could jeopardize Regiment Securities' licenses. And the rising costs of digital marketing made customer acquisition increasingly expensive.
The Tendril Solution: A Compliance-First Technology Partnership
The genius of the solution lay in its careful navigation of FINRA regulations through a consent-based, multi-layered approach. Rather than attempting to automate outbound communications directly (which would create significant compliance risks for a Registered Representative) the system started with inbound lead capture.
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Regiment Securities' marketing materials prominently featured a phone number that connected prospects to "Mo Money," the AI agent that handled initial qualification conversations.
This inbound-first design was legally crucial. Because prospects initiated contact voluntarily, all subsequent communications were consent-based and defensible under regulatory scrutiny.
The AI captured basic information: phone, email, investment interests, and qualification data, and automatically populated Regiment Securities' HubSpot CRM. But the AI didn't make outbound calls, avoiding the regulatory "gray area" that concerned Cavanaugh.
This is where Tendril's role became critical. Tendril's team received the warm, AI-qualified leads through the HubSpot integration and conducted compliant human-initiated follow-up calls.
The Tendril agents could reference the prospect's initial AI interaction, creating immediate context and rapport while maintaining the human control over communications that FINRA regulations effectively require for Registered Representatives.
This human-in-the-loop approach provided the regulatory protection Regiment Securities needed while delivering the scale and efficiency that manual methods couldn't achieve.
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The technology stack created a seamless workflow: prospects called the AI agent and provided qualification information. The data flowed automatically into HubSpot. Tendril's agents received these warm leads and conducted outbound calls with full context about the initial AI interaction. Call outcomes were logged back into the CRM, and high-value prospects were routed to Cavanaugh for closing conversations.
Every interaction was documented, creating the comprehensive audit trail necessary for FINRA compliance.
The Results: From 5 Conversations to 14 in a Single Hour
When Cavanaugh first tested the integrated system with Tendril, the results exceeded his expectations so dramatically that it represented a fundamental turning point for the business.
A single hour demonstrated the system's transformative potential. Fourteen meaningful conversations, nearly three times Cavanaugh's previous daily target, accomplished in just 60 minutes.
The mathematics of this transformation were remarkable:
Traditional Manual Method:
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5 meaningful conversations per full day of chairman time
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25 conversations per week maximum
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Approximately 100 conversations per month at peak capacity
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Growth limited by individual human capacity
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100% of executive time consumed by prospecting
AI-Tendril Enhanced System:
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14 meaningful conversations per hour
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112 conversations achievable per 8-hour day equivalent
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560 conversations per week potential
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2,240 conversations per month theoretical maximum
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Minimal executive oversight required, time freed for strategic activities
The transformation wasn't just about volume, since the quality improved significantly. Tendril was working exclusively with prospects who had already engaged with the AI and expressed genuine interest. These weren't cold calls; they were warm follow-ups with qualified leads who had volunteered their information.
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With just two hours of weekly Tendril engagement, Regiment Securities could generate sufficient qualified conversations to meet their growth targets.
"We figured it out, we just use Tendril Connect 2 hours a week, and we get 30 meaningful conversations, which covers our formula for success," Cavanaugh explains.
With just two hours of weekly Tendril engagement, Regiment Securities could generate sufficient qualified conversations to meet their growth targets.
The system freed Cavanaugh to focus on strategic activities. "It's forcing us to think of ways to become more operationally efficient, and save money, but at the same time it's about freeing our time to have bigger conversations in person, with agents filling the funnel," he notes.
Instead of spending days making low-level prospecting calls, Cavanaugh could focus on strategic partnerships, high-value client relationships, and business development that actually required his expertise.
Capital Raise Campaign: Proving ROI with Real Results
Validation came through the first campaign ever!
A focused campaign targeting 50 attendees from a Regiment Securities networking event. These warm prospects had already demonstrated interest by attending and had some familiarity with the brand.
Tendril executed a targeted calling campaign, with agents referencing both event participation and any subsequent AI interactions. The focused nature allowed for clear measurement of results and concrete insight into ROI potential.
Campaign Parameters & Results:
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Target Audience: 50 previous event attendees (warm prospects)
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Investment Secured: One engagement resulted in new investor participation
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and measurable revenue contribution.
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Commission Earned: $5,000 (at Regiment's standard 5% rate)
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Overhead: Minimal technology and service costs
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Scalability Proof: If 50 prospects generated $5,000, larger campaigns promised exponentially greater returns
The campaign delivered remarkable financial results from a relatively small target list. From those 50 prospects, Tendril's efforts directly contributed to securing new investor participation and measurable revenue contribution investment from a single qualified lead. Using Regiment Securities' standard 5% commission structure common in broker-dealer capital raising, this single success generated $5,000 in immediate revenue for the firm.
That’s $5,000 in immediate revenue with just 1 hour of Tendril Connect.
"I had almost no overhead," Cavanaugh emphasizes. "Right now we've just used Tendril to reach out to investors. We're gonna start using it for issuer outreach, clients."
The success proved the model was replicable and scalable. The system had demonstrated the ability to generate high-value results with minimal overhead investment.
More importantly, the success validated the entire strategic approach. The combination of inbound AI qualification, human-powered calling with warm context, and regulatory compliance had proven itself with real dollars and actual investments.
Business Model Evolution: Achieving Software Company Economics
The partnership with Tendril fundamentally altered Regiment Securities' business economics. Traditional broker-dealer operations carry significant fixed costs: sales staff salaries, extensive training programs, compliance personnel, and overhead.
The Tendril model inverted this cost structure.
Tendril Enhanced Model:
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Low fixed costs (technology subscriptions, service fees)
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Exponential scaling potential (growth driven by marketing spend, not headcount)
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Executive time focused on strategic, high-value activities
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Software company-like margins (90%+ when optimized)
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This comparison reflects a genuine transformation in operations. Software companies achieve exceptional margins because they can serve additional customers with minimal incremental cost. The AI enhanced, human powered Tendril system created similar dynamics: once the infrastructure was in place, generating additional leads and conversations required minimal additional investment.
The economic shift enabled strategic focus on high-margin activities. Instead of Regiment Securities' team spending time on low-value prospecting, they could concentrate exclusively on relationship building, deal structuring, and client service.
Expanding the Vision: From Investors to Issuers and Beyond
The initial success with investor outreach quickly revealed broader applications. While Regiment Securities started by using Tendril to reach potential investors, Cavanaugh recognized the same approach could transform their issuer outreach as well.
"Right now we've just used Tendril to reach out to investors. We're gonna start using it for issuer outreach, clients," Cavanaugh notes.
In the capital raising business, finding companies that need capital is just as important as finding investors who can provide it.
Expansion Opportunities:
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Multiple Simultaneous Campaigns: Parallel efforts targeting different investor segments, issuer categories, and geographic markets
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Issuer Prospecting: Qualifying companies with genuine capital needs using the same AI-Tendril approach
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Geographic Expansion: Scaling beyond current regional focus to national reach
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Service Line Extension: Applying the model to additional Regiment Securities offerings
Cavanaugh's most ambitious vision extends to massive marketing amplification that would have been inconceivable under the traditional manual model. "I want to put a picture of our AI guy with his phone number on the billboard in Times Square. 'Call Mo!' We're going to go plaid here when we figure that side of it out," he declares.
The Times Square billboard vision represents a fundamental understanding of how the economics have changed. In the traditional model, massive marketing spend would be wasteful because the firm couldn't follow up with leads generated. But with AI handling initial qualification and Tendril providing scalable human follow-up, Regiment Securities could actually capitalize on large-scale marketing in ways previously impossible.
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Join the Future of Financial Services Sales
The transformation at Regiment Securities provides a blueprint for how regulated industries can achieve technology company-like efficiency while maintaining complete compliance.
The Results:
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2,240% increase in meaningful conversation capacity
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Reduced fix costs, approaching software company economics
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Proven ROI through real investment generation ($5,000 in revenue from a single 1 hour campaign)
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Scalable model ready for exponential growth across multiple applications
Perhaps most importantly, the case proves that regulatory compliance and technological innovation are not mutually exclusive. With careful planning, strategic partnerships, and compliance-first thinking, regulated industries can achieve the same efficiency gains and growth potential as their unregulated counterparts.
If your team is facing similar challenges, and you want to get some free time back in your calendar to do high-level ultra focused activities, Tendril can help you achieve similar results.
Whether you're in financial services, healthcare, legal services, insurance, or any other regulated industry, our human-powered calling service integrates seamlessly with your existing systems to deliver qualified conversations at scale.
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What You'll Get with Tendril:
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Scalable human-powered calling that maintains compliance and quality
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Seamless integration with your CRM and lead generation systems
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Warm, contextual conversations that convert better than cold outreach
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Proven results with measurable ROI from day one
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Expert guidance from a team that understands regulated industries
Stop letting human capacity limit your growth. Learn how technology-enabled processes, when properly supervised, can improve operational efficiency while maintaining compliance.
Schedule your demo today and discover what's possible when technology meets human expertise.
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