In this episode of The Marketing Phoenix Podcast, host Melissa “Rogo” Rogozinski sits down with Stephen Embry, founder of TechLaw Crossroads and respected voice in legal technology, to unpack why so many startups miss the mark with their messaging.

They explore how sales teams and sales reps in legal tech can create more effective sales conversations by truly understanding customer pain points and aligning their message with how law firms actually operate. From actively listening during every sales call to using evidence-based sales strategy, Melissa and Steve show how to build trust, not just a pitch.

What You’ll Learn:

• Why your product or service messaging should reflect their business, not yours
• How to tailor your sales process to match how law firms make decisions
• How sales reps can use open-ended questions to uncover true customers’ pain
• Why actively listening builds rapport and creates more effective sales conversations
• How evidence-based messaging helps your software solution stand out in legal technology
• Tips for building real-time connections that improve customer experiences

Whether you are going to a legal tech conference or changing your sales strategy, this episode can help. It shows you how your team can communicate, sell, and connect with potential clients in the legal field.

Connect with Stephen Embry on LinkedIn.

Chapter Titles:

01:21 – Introducing Stephen Embry of TechLaw Crossroads
03:13 – How Harvey Won Big Law and Became a Unicorn
06:45 – Avoiding Common Messaging Mistakes With Modern Buyers
09:04 – Showing Evidence Over Marketing Jargon in Law Firm Sales
12:28 – Chasing AmLaw Firms Misses 80% of the Market
17:33 – “Saving Time” Fails as a Messaging Strategy
18:59 – Applying Jevons Paradox to Legal Tech Growth
22:10 – Adapting Messaging to Evolving Legal Buyer Behavior
26:16 – Delivering Real Solutions Instead of Future Promises
29:37 – Using Content to Build Trust and Authority
32:49 – Iterating Content Strategy With Sales Every Quarter
34:50 – Learning Buyer Needs Directly at Lawyer Conferences
36:36 – Building Trust and Opportunity at Local Bar Events
41:15 – Build Credibility Beyond Vendor-Only Messaging
46:17 – Demonstrating AI Solutions by Solving Real Pain Points
48:38 – Replace Buzzwords with Buyer-Centric Language
52:03 – Sharing Tips to Get Your Messaging Right

SEO Keywords: solution selling, customer pain points, legal tech, sales conversations, law and technology, legal tech conference

Connect with The Marketing Phoenix Podcast

• Subscribe on Your Favorite Podcast Platform
• Connect on LinkedIn
• RPC Strategies' Website

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• The Proven Sales Email Codex
• The AI Security Questionnaire
• Our Tailored Growth Services

Many legal tech and B2B companies struggle to move prospects through the sales cycle. When sales reps walk into sales calls without preparation or rely only on marketing to deliver leads they miss opportunities for closed deals and stronger customer relationships.

Episode Overview:

In this episode of the Marketing Phoenix Podcast, host Melissa “Rogo” Rogozinski welcomes Chris Cangero, founder and CEO of DocStyle. Chris shares his entrepreneurial journey and explains why so many legal tech startups and law firm vendors face challenges with client acquisition and customer base growth.

The conversation highlights how sales reps can improve discovery call, refine sales conversations, and use consultative selling to build trust with decision makers. They also discuss how aligning sales strategy with targeted marketing, buyer personas, and case studies helps create a more customer-centric approach that drives higher conversion rates.

What You’ll Learn:

• Why legal tech sales cycles are longer—and how to adapt your sales strategy
• The dangers of winging a sales pitch vs. preparing for discovery call
• How discovery calls fuel solution selling success
• Why sales and marketing must align for client acquisition
• Tips for using marketing collateral to reinforce selling strategies

Connect with Chris Cangero on LinkedIn.

Connect with The Marketing Phoenix Podcast

• Subscribe on Your Favorite Podcast Platform
• Connect on LinkedIn
• RPC Strategies' Website

***DOWNLOAD FREE RESOURCES***

• The Proven Sales Email Codex
• The AI Security Questionnaire
• Our Tailored Growth Services

Cold outreach sucks. For most law firm buyers, cold emails without context are an instant delete.

Legal tech startups and B2B sales teams can’t afford to waste time on outdated sales approaches. The good news? Outbound sales feels different when sales reps use marketing insights, consultative selling, and solution selling strategies that build trust with decision makers.

In this episode of The Marketing Phoenix Podcast, Melissa “Rogo” Rogozinski shows why cold outreach fails and shares practical ways to fix it. She shares insights from law firm buyers and seasoned sales leaders in legal tech who know exactly what works and what doesn’t.

If you’re building a growth marketing strategy, you’ll learn how sales and marketing alignment helps sales professionals transform a generic sales pitch into open-ended questions that engage the target audience. By actively listening and building rapport, sales reps can guide buyers through the customer journey, strengthen the sales funnel, and generate leads that actually convert.

What You’ll Learn in This Episode:

• Why cold emails without context = instant delete
• How marketing insights fuel consultative selling and improve sales performance
• Outbound sales strategies that feel relevant, not random
• The role of patience in long legal tech sales cycles
• How LinkedIn outreach builds rapport with decision makers before the first call
• Proven steps to increase conversion rates, grow your customer base, and strengthen the sales pipeline

Podcasts with Emily, Mari, Corey, and Chris:

Persona Fatigue: Sell to Problems, Not Titles

Research Like a Pro to Close More B2B Sales Deals

Prepping Smarter & Closing Faster (in Legal Tech Sales)

Connect with The Marketing Phoenix Podcast

• Subscribe on Your Favorite Podcast Platform
• Connect on LinkedIn
• RPC Strategies' Website

***DOWNLOAD FREE RESOURCES***

• The Proven Sales Email Codex
• The AI Security Questionnaire
• Our Tailored Growth Services