How David Cherrie and Arcade Are Scaling Top Sales Leadership with AI Across Retail Chains

David Cherrie and Arcade’s New AI Sales Leader Platform

David Cherrie noticed a recurring pattern in retail: one manager leads a top-performing store while others lag behind. Now, as CEO and co-founder of Dallas-based Arcade, he’s launching tools to replicate the behaviors that make top managers successful across all locations. This August, Arcade acquired Upduo, an AI-powered coaching platform, and introduced Arcade AI Sales Leader.

“The success of any retail location starts and ends with the quality of its manager,” Cherrie said. He identified a common challenge for retail executives: how to capture the qualities of a top sales leader and deploy that excellence everywhere. The acquisition was an all-cash deal supported by new and existing investors, with details undisclosed.

Unlike traditional learning systems, Upduo was created specifically for retail’s fast-paced environment, high turnover, and constant distractions. It was built from the ground up as an AI-focused coaching engine. Cherrie believes the gap between top sales leaders and others isn’t just about motivation—it’s also about skill. Employees need both the desire and the ability to succeed.

Arcade has long emphasized motivation through gamification and incentives, engaging frontline retail workers. The Upduo acquisition adds skill development to this, aiming to “turn every field manager into your best sales leader.”

Growth Driven by Enterprise Demand

Arcade has recorded back-to-back revenue highs in 2024. Their client list includes Cricket Wireless, Metro by T-Mobile, Motorola, Spectrum, Dish, and AT&T. Since relaunching post-COVID in early 2023, Arcade serves over 20,000 paid users across hundreds of retail organizations, ranging from single stores to enterprises with over 2,000 locations.

The platform has facilitated 150,000 hours of sales role-play and 2 million one-on-one coaching sessions. Arcade’s method scales sales training without the need for costly coaches. Top performers train mid-level employees, who then coach new hires—reducing the workload on managers and closing the performance gap.

Arcade’s core platform uses gamification and micro-incentives to focus sales teams on revenue-driving activities rather than traditional leaderboards. The SaaS pricing varies by user or store. The new AI sales features are available as upgrades, combining motivation and skill training into one platform.

Adam Rogers of Next Coast Ventures praised the acquisition, noting Arcade’s forward-thinking use of AI to deliver more value.

Strategic Acquisition to Accelerate Growth

Cherrie explained that choosing to acquire Upduo instead of building AI capabilities from scratch was about speed. Upduo already had a retail-native, AI-first platform. Both companies shared customers who were already using Arcade to motivate Upduo usage, confirming the value of integrating their solutions and opening cross-selling opportunities.

Top retail customers focus on developing field managers first, then frontline teams. They combine Arcade’s gamification with consistent coaching. This pattern highlighted the need for a unified solution.

Scaling Skill Development Across Retail

Wei Sun, Upduo’s co-founder and now Arcade’s chief technology officer, said the deal fulfills their original vision: using AI to make skill development more effective and accessible. Joining Arcade allows them to scale that vision widely.

The combined AI Sales Leader platform creates a virtuous cycle: employees reinforce their skills by training others, with coaching sessions tailored to business metrics. This setup ensures consistent quality across locations—whether a new hire is in Dallas or Detroit. Managers spend less time on paperwork and more on selling, as AI handles assessments and follow-ups. Employees can practice skills during slow periods to improve weekend sales.

The Technology Powering AI Sales Leader

From the moment an employee opens the app via one-tap sign-in, AI guides their development—assessing skills, assigning training, pairing them with peer coaches, and tracking progress. The platform includes several AI components:

• Coach AI: Guides managers through coaching conversations, records sessions, and acts as a virtual assistant when managers are unavailable.
• Train AI: Provides role-play scenarios for skill-building.
• Certify AI: Verifies employees’ skills before they engage with customers.
• Gamified AI: Personalizes challenges to keep employees engaged.
• Automated Scorecards: Instantly grade sessions and highlight areas for improvement.

Together, these tools form a “virtual management layer” that never tires, reducing administrative tasks and managing training assignments efficiently.

Overcoming Retail’s Adoption Challenges

Cherrie identified three major hurdles for tech adoption in retail: dispersed teams, employee fatigue from too many tools, and high turnover. Employees often don’t have spare time to learn new workflows.

Arcade’s rollout starts by training market leaders to help onboard store managers, then aims to get 100% of employees onboarded within the first 10 days. The platform emphasizes the “WIIFM” (What’s In It For Me) factor, ensuring users see clear benefits from the start. Features like single sign-on and a gamified onboarding flow reduce friction and help all employees, regardless of tech experience, get on board quickly.

Looking Ahead: A Global Vision

Arcade was founded in Australia by David Cherrie and James McLaren, who serves as Principal Engineer. The company opened a Dallas office in 2016 after graduating from the REVTECH accelerator, attracted by strong customer and talent access. In 2024, Mark Clare joined as head of sales, supporting the company’s growth into specialty retail markets.

With AI Sales Leader, Arcade positions itself in a competitive space blending sales coaching, enablement, and learning tools. The company plans to focus on AI sales solutions for desk-less sales organizations, including retail, car dealerships, and door-to-door sales teams. International expansion and a strategic exit are also in the plans.

For sales professionals interested in AI-driven sales training and coaching solutions, exploring AI tools and courses can further enhance skills and effectiveness. Resources like Complete AI Training's latest courses offer valuable insights into AI applications for sales roles.