Guerrilla Marketing, SEO, and AI—Marketing That Works w/Derek Boggs

Derek Boggs, a veteran marketer with a proven track record spanning industries from B2B SaaS to physical security, recently appeared on the GTM Secrets podcast hosted by Stephen Lowisz. Derek’s career path, characterized by bold transitions, innovative strategies, and customer-first thinking, offers a treasure trove of valuable lessons for marketers tackling complex challenges.

From building trust with hard-to-reach audiences to driving demand with cutting-edge AI tools and creative campaigns, Derek’s approach to scaling revenue is nothing short of extraordinary. Below, we break down the key strategies, practical implementations, and actionable steps shared during the podcast.

Mastering the Transition Between Industries

Transitioning between wildly different industries is challenging for any marketer, but Derek has navigated it with surgical precision. Moving from marketing to sales-heavy tech audiences at SaaS companies to tackling the concerns of physical security professionals required a complete overhaul in strategy, tone, and tactics.

For example, when marketing to sales and marketing professionals, Derek’s focus was on ROI metrics, productivity gains, and social proof. However, physical security professionals are more mission-driven, focusing on tangible solutions to protect people and property.

Steps for Successful Transitions

  1. Understand the Persona with Laser Focus
    • Interview existing customers, analyze pain points, and immerse yourself in the day-to-day realities of their world.
    • For Derek, this meant deeply empathizing with security professionals’ needs, particularly when their decisions impact critical areas like safety and asset protection.
  2. Adapt the Message
    • Take your audience’s unique motivators into account when crafting messages. Derek and his team don’t oversell to their physical security audience. Instead, they position their product as a partner in solving problems. For instance, instead of selling “features,” they highlight outcomes like reducing theft or improving on-site safety.
  3. Leverage Existing Trust Factors
    • Use client testimonials, peer case studies, and third-party validation to build initial credibility. Derek ensures each sales call or ad is backed by examples of how peers in the industry successfully used LVT’s solutions.
  4. Experiment in New Channels
    • Explore where your new audience engages. Derek knew LinkedIn wasn’t a hotbed for physical security professionals, so his team invested heavily in trade shows, direct engagements, and targeted digital ads to make up for that gap.

Example in Action

When entering the physical security space, Derek found that many security professionals were ex-security guards or had mission-driven motives. They weren’t interested in a flashy pitch. That’s where sending free product pilots, attending specialized events, and tailoring messaging became critical to connecting.

Innovations in Building Trust with Pilots and Trade Shows

One standout tactic in Derek’s arsenal is the use of free pilots. When selling high-value physical hardware, customers often hesitate to commit without seeing results. Derek’s response? De-risk the buying process.

By allowing prospects to test solutions in their most challenging environments — parking lots with chronic theft, high-risk construction sites — they could see the product's tangible value firsthand. Providing results without upfront investment helped LVT quickly gain trust with even the most skeptical buyers.

At the same time, Derek recognized the value of face-to-face connections, especially in an industry like physical security. Trade shows became a touchpoint for real conversations, giving his team opportunities to showcase the product live and build rapport with key decision-makers.

Tactical Takeaways

  1. Launch Risk-Free Pilots
    • Implement short-term trial solutions for customers. Use product performance data to justify the sale.
    • Example metric to track: Performance uplift during the pilot. For instance, measure reductions in incidents like break-ins during the trial period.
  2. Maximize Trade Show ROI
    • Prepare pre-event campaigns to schedule meetings during the show.
    • Invest in eye-catching product displays and hands-on demos. LVT showcases their mobile security solutions prominently, turning trade show attendees into advocates.
  3. Follow the Data
    • Gathering feedback during pilots and at trade shows can inform future product improvements or marketing angles. Derek’s team continuously integrates customer stories into case studies to fuel sales efforts.

Demand Gen Mastery and Digital Advertising Excellence

Demand generation is the beating heart of Derek’s strategy. When Derek first joined LVT, his team primarily worked with small businesses, targeting local high-intent searches. Over time, they calibrated their focus to larger enterprises through more strategic demand gen techniques. Today, 60% of their marketing-driven revenue stems from enterprise accounts — a huge shift from their SMB-heavy beginnings.

Tactical Digital Advertising Strategies

Derek’s team runs a full-funnel digital advertising strategy that blends paid, organic, and intent-first approaches.

Paid Search

  • Google Ads serve as a primary driver for high-intent conversions. LVT bids aggressively on long-tail keywords like “construction site security” or “cost of unarmed guards.” Since their product directly competes with traditional security solutions, these ads position their mobile security unit as a cost-effective, innovative alternative.

Meta Advertising

  • Derek’s team doesn’t shy away from perceived “non-B2B” channels like Meta (formerly Facebook). Retargeting works especially well here. For instance, a prospect who visits their site after searching for traditional security solutions on Google will be served ads showcasing LVT’s mobile units alongside competitors for cost comparison.

PMAX Campaigns

  • Performance Max campaigns on Google allow Derek’s team to display ads across varied placements, from YouTube pre-rolls to Gmail banners, targeting users who have visited competitors’ websites.

The Unexpected Star of the Show? AI

Scaling high-performing content has been critical for Derek’s success. His team publishes up to five blogs per week, providing helpful articles for searchable terms like “organized retail crime solutions.” With AI-powered tools like Jasper or ChatGPT, they draft articles, outlines, and even email campaigns faster, freeing up human marketers to focus on polishing the final product.

Tactical Metrics to Monitor

  • Search Conversion Rates (Target > 8%)
  • Cost per Click (CPC) on Meta or Google campaigns (Target <$2 for small business leads, <$20 for enterprise traffic)
  • Blog Organic Traffic Lift per quarter (Target 15% YoY growth)

Rethinking Channel Mix & Demand Challenges

Stale channels can stifle growth. That’s why Derek constantly experiments with new sources of traffic. His team has begun looking at Reddit ads — an untapped resource for LVT’s highly niche personas. Additionally, they’re expanding partnerships with associations and publications, offering thought leadership and co-branded webinars.

Tactical Approach to Diversification

  1. Pilot New Channels
    • Example Derek is testing next? Reddit ads. While niche, Reddit offers cheap CPCs, ideal for AB testing messaging for emerging concerns like organized retail crime.
  2. Partner for Borrowed Trust
    Instead of spending years building certain audiences, Derek’s team partners with associations and top publishers in the field, publishing sponsored articles or running collaborative events.
  3. ZoomInfo for Intent-Driven ABM
    Identifying high-intent accounts allows Derek’s SDRs to deploy hyper-specific ABM campaigns. For example, if a lead searches “cost of security management systems,” LVT reps immediately follow up with insights tailored to their needs.

ABM Gone Bold

Not all ABM campaigns are equal. One memorable initiative involved sending custom pillows to security professionals. Since many of Derek’s customers lose sleep over their high-stakes roles, the pillow carried the message, “We’ll help you rest easy.” Coupled with digital, email, and phone touches, this campaign saw massive conversion rates.

Pro Tip
Personalized campaigns shouldn’t stop at gifts — craft empathetic copy aligned with their job stressors. Derek’s playbook? Messaging, “LVT doesn’t fall asleep on the job,” resonated with buyers.

Advice and Action for Marketers

Derek’s phenomenal success scaling LVT from $15M to $250M ARR underscores the power of relentless adaptation, customer-focused strategies, and cross-channel excellence.

Here’s how you can channel Derek’s playbook into your role:

  1. Do Double Discovery
    • Interview clients AND their customers. Understand second-order benefits your product delivers. (e.g., Safer environments = fewer lawsuits.)
  2. Use Intent Wisely
    • Prioritize accounts showing early interest with ABM sprints, blending gifting, sales outreach, and personalized follow-ups.
  3. Test AI Everywhere
    • Whether automating the first draft of blogs or creating database-specific ad creatives, use AI tools like Jasper for efficiency without losing quality.
  4. Always Know What’s Next
    • Derek’s pivot to Reddit, publications, and tactile ABM gifts proves experimentation never ends, even in a winning strategy.

With these lessons, you’re ready to dominate your next campaign — turning even the hardest-to-reach audiences into loyal evangelists.