From High Deductible Workers’ Comp to Scalable Growth: How Insurance Agency Can Leverage Alternative Risk, Virtual Teams, and Marketing Automation – A Conversation with Eric Stein
From High Deductible Workers’ Comp to Scalable Growth: How Insurance Agency Can Leverage Alternative Risk, Virtual Teams, and Marketing Automation – A Conversation with Eric Stein
The commercial insurance industry is undergoing a transformation, especially for agencies working in the middle market. As traditional models face increasing pressure from rate hikes, market consolidation, and technology shifts, savvy agency owners and producers are finding new ways to grow, scale, and protect their margins.
Three key strategies are rising to the top: implementing alternative workers’ compensation programs, building virtual insurance teams, and using marketing automation to create sustainable lead pipelines.
In this post, we’ll walk through each of these pillars and share real-world insights on how to incorporate them into your agency. Whether you’re an agency principal, sales leader, or producer, this blueprint will help you adapt to modern challenges while building long-term value.
Understanding the Landscape of Workers' Compensation Alternatives
Workers’ compensation insurance is often one of the largest cost centers for businesses—making it a huge opportunity for agents who know how to position alternatives to guaranteed cost programs. But there’s a big gap between knowing the lingo and actually helping a client transition into more complex risk financing.
Before jumping into captives, it’s critical to understand the stepping stones:
- Guaranteed Cost: The most basic structure. Clients pay a fixed premium regardless of losses.
- Retro Plans: A hybrid model where the client’s final premium adjusts based on losses.
- High Deductible Programs: Clients retain more risk upfront, often requiring significant collateral.
- Captive Insurance: Self-insurance models where the client becomes the carrier and assumes full or partial risk.
“Captives are not something you dabble in. You either do them or you don’t.” – David Carothers
When Is a Client Ready for a Captive?
Captives are not for everyone. They’re best suited for financially stable companies with strong risk management practices and the ability to commit capital long term. Many agents make the mistake of recommending a captive purely to save on premium—without considering whether the business has the operational infrastructure to support it.
Instead, producers should guide clients through a gradual risk transition, often starting with a high deductible workers’ compensation program. This not only prepares the client but also provides a proving ground for how well they can manage claims and safety protocols.
“You’re not a broker anymore. You have to run it like an insurance carrier.” – Eric Stein
Building a Risk Management-Centric Sales Strategy
Clients that thrive in alternative comp programs are the ones who treat risk management as a priority, not an afterthought. That’s why producers need to shift their positioning from “insurance seller” to “trusted risk advisor.”
To be successful, your agency should help clients implement:
- Return-to-work programs
- Injury triage and nurse hotlines
- Field-level safety training
- Custom risk assessments
- Actuarial support for setting realistic loss picks
These strategies don’t just reduce claims—they also allow clients to retain more risk with confidence, opening the door for self-insurance, captives, or risk-sharing pools down the road.
Scaling Operations with Virtual Assistants in Insurance
Scaling an insurance agency doesn’t always mean hiring more people in-house. In fact, many successful agencies are doing the opposite: building hybrid teams using virtual assistants and remote professionals to handle repetitive and operational tasks.
“My mantra was outsource and automate.” – Eric Stein
Eric Stein, founder of Insured Solutions, scaled his agency by outsourcing tasks to offshore teams in India and the Philippines as early as 2009. While many agencies are just now exploring the use of remote insurance professionals, Stein was already using VAs to handle back-office operations, appointment setting, and data entry.
Where to Start with Virtual Assistants
If you’re just getting started with outsourcing, consider offloading the following:
- Submission entry into CRMs or agency management systems
- Quote requests and carrier follow-ups
- Renewal preparation
- COI requests
- Appointment setting and lead generation
“You have to treat virtual professionals like real employees—train them, support them, and manage them like your in-house team.” – David Carothers
The key is to pair your virtual team with a U.S.-based point of contact who can supervise, handle feedback, and resolve issues quickly. This keeps your domestic staff focused on client experience and selling—while the VAs take care of the heavy lifting.
Documenting Workflows: Your Key to Offshore Success
Many agencies fail with virtual teams not because the people are unqualified, but because there are no documented workflows in place. This leads to confusion, errors, and frustration.
Here’s how to fix that:
- Use tools like Tango to record your screen as you perform tasks. It generates step-by-step guides with screenshots automatically.
- Supplement with Loom videos for visual learners.
- Store all resources in a Learning Management System (LMS) so your new hires can self-train over 30–90 days.
- Start with 1–2 offshore team members and build from there.
“If you’re handing someone a script and a call list with no process or feedback loop, you’re setting them up to fail.” – David Carothers
Lead Generation at Scale with Marketing Automation
If your producers are spending all their time chasing cold leads or begging for referrals, you’ve got a lead problem—not a sales problem.
That’s where marketing automation becomes a game-changer.
What Marketing Automation Can Do for You
- Drip campaigns to warm up cold prospects
- Lead scoring to prioritize follow-up
- Nurture sequences based on behavior
- Integration with CRMs for real-time engagement
- Scalable outreach across email, social media, and SMS
“I built a lead engine where producers didn’t have to cold call. Appointments came in through automation, telemarketing, and email.” – Eric Stein
Stein started small, testing email blasts to a few hundred contacts. Once the messaging worked, he scaled to over 80,000 contacts at the push of a button. Today, platforms like AgencyZoom, HubSpot, and GoHighLevel make it easier than ever to automate campaigns without breaking the bank.
Leveraging Cost Efficiency to Attract Top Talent
One unexpected benefit of outsourcing and automation? You get the margin flexibility to pay top dollar for top talent.
Eric Stein used offshore teams to save on labor and then reinvested those savings into six-figure salaries for producers, underwriters, and CSRs. That allowed him to recruit people who wouldn’t have considered a startup or boutique agency otherwise.
It also enabled him to scale fast without bloating overhead, a crucial factor in eventually selling part of his firm to private equity.
Final Thoughts: Are You Ready to Evolve?
This isn’t about shiny objects or fads—it’s about adapting to the modern insurance marketplace. If you’re serious about scaling your agency, protecting your margins, and building something that lasts, the combination of alternative risk strategies, virtual teams, and automation is a playbook worth following.
Before you jump in, ask yourself:
- Do we have documented workflows for every core process?
- Are we building a proactive risk management culture?
- Can we train and manage remote professionals effectively?
- Is our lead generation predictable and scalable?
If the answer is no to any of these, you’ve got work to do. But the good news is, the roadmap exists—and with the right focus, your agency can thrive in today’s evolving market.
Why Employee Ownership is the Key to Sustainable Agency Growth and Talent Retention
In an increasingly competitive commercial insurance landscape, agency owners are struggling to find long-term solutions for succession planning, talent retention, and business perpetuation. Many have considered private equity sales, others offer limited equity to top producers—but a growing number are discovering a more powerful alternative: the Employee Stock Ownership Plan (ESOP).
Captive Insurance as a Business Continuity Plan: How Strategic Advisors Protect and Grow Their Book of Business
In today’s competitive commercial insurance market, your book of business is under constant attack. Competitors are targeting your best accounts every day, just like cybercriminals probing a website for vulnerabilities. If you don’t have a plan to defend and grow your client relationships, you’re leaving yourself exposed.
How to Reverse Engineer Your Sales Funnel and Crush Your Q4 Insurance Production Goals
As we enter the fourth quarter, many commercial insurance producers begin to panic. Whether you’re behind on your goals or just trying to hit that final sprint, the Q4 crunch is real. But the producers who consistently win don’t treat Q4 as a Hail Mary. They plan with precision, reverse engineer their goals, and execute with ruthless consistency.
In this post, we’ll break down how you can reverse engineer your sales funnel, identify your revenue gaps, and finish the year stronger than you started. Whether you’re writing workers’ comp or cyber liability, these strategies apply across all middle market verticals.
Captive Insurance Fundamentals: How Business Owners Can Retain Risk, Keep Profits, and Control Their Future
In the commercial insurance world, most producers are laser-focused on finding the best premium and coverage from traditional carriers. But there’s a powerful alternative that can help the right business owners keep more control over their risk, retain underwriting profits, and create a long-term competitive advantage.
Mastering Wholesale Partnerships: Submission Strategies, Underwriter Relationships, and Technology Tools for Middle-Market Success
In today’s competitive insurance marketplace, middle-market agencies must leverage every available advantage to win and retain business. One of the most underutilized yet powerful resources at an agent’s disposal is the wholesale market. By establishing strong partnerships with wholesalers, agents can access capacity, expertise, and proprietary programs that are often unavailable through direct channels. However, success in the wholesale arena requires more than simply submitting risks and hoping for the best.
How AI-Powered Workflows Are Transforming Sales, Marketing, and Client Communication
In the fast-paced world of commercial insurance, where every hour counts and every interaction matters, producers and agency owners are turning to artificial intelligence not as a replacement for human connection—but as a force multiplier. AI tools like ChatGPT are no longer just novelties or futuristic concepts. They are strategic business assets, helping commercial producers streamline workflows, scale personalization, and reclaim valuable time.
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