Scaling influence & embracing AI: Lacey Lundschen on the future of enterprise sales

In this enlightening episode of Wintage Club Conversations, we dive deep into the world of technical sales leadership with Lacey Lundschen, VP of Enterprise and Mid-market Sales at Docker. From her journey in sales to her insights on AI's impact on the industry, Lacey shares valuable perspectives that resonate with both sales professionals and technical leaders alike.

The path to sales leadership

Lacey revealed that her career began unexpectedly during college while working at AT&T selling phones. "I never planned to be in sales," she admits. "But I discovered I had a natural ability to understand people's needs and match them with solutions."

This talent led her to Rackspace as an SDR, where she quickly distinguished herself by moving to full-cycle selling within just 12 months. From there, her trajectory took her through notable roles at Dialpad, MongoDB as Regional Director, and Starburst as Regional VP, before landing at Docker.

Her pivotal moment came during her time at Rackspace, where she realized she could combine her interest in technology with her ability to build relationships. That's when she knew sales would be her long-term career path.

As for critical skills that contributed to her success, Lacey emphasizes:

• Genuine curiosity: "Sales frameworks are helpful, but nothing replaces authentic interest in your customer's challenges."
• Active listening: "Technical buyers can immediately tell if you're just waiting for your turn to speak."
• Adaptability: "The tech landscape changes rapidly. You need to be comfortable with uncertainty."
• Cross-functional collaboration: "Building strong relationships between sales and product/engineering teams is essential for credibility."

The unique challenge of technical sales

When discussing the challenges of selling to B2B CTOs and hands-on engineers, Lacey offers a refreshingly honest perspective: "Engineers often understand our products better than some of our sales team members. You simply cannot fake expertise with these buyers."

Her approach involves several strategic elements:

1. Slowing down the process: "With technical buyers, rushing to solutions undermines credibility. We focus heavily on qualification and discovery."
2. Understanding the 'why' behind technical questions: "I constantly teach my sales rep to deep dive into the product and listen carefully because when an engineer asks about orchestration capabilities, they're often trying to determine if our solution will integrate with their existing systems."
3. Building different business cases for different personas: "We segment stakeholders into three categories: technical implementers, technical decision makers, and business decision-makers. Each requires a different approach."

Equipping teams with technical proficiency

Leading sales at a company like Docker presents unique challenges, particularly in ensuring sales teams possess sufficient technical knowledge. Lacey's method centers around three critical factors. 

First, at Docker, they've implemented a comprehensive technical certification program that all sales team members must complete. This program is continuously updated as their platform evolves, ensuring the sales team always has current knowledge about Docker's capabilities and technical advantages.

Second, Lacey has also established strong communication channels between Docker's product/engineering teams and the sales organization. Engineers regularly join sales calls, provide feedback, and help translate complex technical concepts into business value for customers.

Third and last, Docker has created specialized roles for technically-minded sales professionals who serve as bridges between pure engineering and pure sales. These individuals have deeper technical understanding while maintaining strong sales skills, allowing them to navigate complex technical discussions while keeping business outcomes in focus.

"The goal isn't for every salesperson to become an engineer," Lacey clarifies. "It's about having enough technical understanding to identify the right problems and bring in the right resources at the right time."

AI's impact on PaaS and sales

As a company serving developers, Docker sits at the intersection of AI innovation and practical application. Lacey sees AI's impact on the Platform-as-a-Service space as transformative.

"AI is fundamentally changing how developers build applications," she notes. At Docker, they've embraced this transformation through several initiatives: their Docker extension for GitHub Copilot, Docker Genie stack for LLM integration, partnership with NVIDIA, Docker Labs Gen AI series, and development of Gordon, their new AI agent currently in early stages.

When it comes to AI's influence on sales strategies, Lacey identifies several key trends. AI is enhancing discovery by helping sales teams identify patterns in customer behavior that might otherwise be missed. It's enabling personalization at scale, allowing teams to customize outreach and follow-up at unprecedented levels. Additionally, predictive analytics powered by AI is transforming sales forecasting from an art to more of a science.

She emphasizes that AI isn't replacing sales professionals but making them more efficient by handling routine tasks and surfacing insights that enhance human decision-making. "The most successful teams will be those that leverage AI as a force multiplier rather than seeing it as a replacement," Lacey observes.

Sales trends for 2025

Looking ahead to 2025, Lacey identifies several trends that sales and revenue leaders should prepare for. The days of the single decision maker are gone, with enterprise deals now regularly involving 8-12 stakeholders forming expanded buying committees. As more companies adopt product-led growth (PLG) models, sales teams need to adapt by adding value beyond what customers can discover on their own.

In the current economic climate, there's an increased focus on demonstrating a clear return on investment. "In a tightening economic environment, buyers need more than promises. They need concrete data showing how your solution will deliver value," Lacey explains.

Additionally, data-driven approaches are becoming essential to every aspect of the sales process. Metrics, analysis, and optimization are no longer optional but fundamental requirements for competitive sales organizations.

Lacey believes these trends will require sales organizations to become more agile, technically proficient, and focused on measurable outcomes as they navigate the evolving landscape of technical sales.

Versatility & curiosity are key to sales success

As Docker continues to expand its footprint in the developer tools space, Lacey Lundschen's balanced approach to technical sales leadership provides valuable lessons for sales professionals across the industry. Her emphasis on genuine curiosity, technical credibility, and adaptability offers a blueprint for success in an increasingly complex B2B sales environment.

"The best sales professionals I've worked with are those who can switch between discussing container orchestration details with a developer one minute and explaining cost savings to a CFO the next," she concludes. "That versatility, combined with genuine curiosity about customer problems, is what drives successful technical sales today."