Arena: AI-Sales Coach
AI-simulated buyer scenarios for reps to practice objections handling, and improve closing skills.
Company:
Clipboard Health
Industry:
Sales
Deliverables:
MVP
Timeline
2025
Diego has been a standout product design partner. He challenges assumptions with thoughtful debate, moves quickly from discovery to clear deliverables, and takes real ownership of direction and decisions. He’s highly collaborative and brings strong AI UX thinking around conversational flows, guardrails, and explainability.
Luiz Lima
Luiz Lima
Luiz Lima
AI Team Lead
AI Team Lead
AI Team Lead
About
Most sales training breaks down at the worst moment: when a rep gets interrupted, challenged, or pushed into a hard objection. The goal with Arena was to make practice feel like a real call, then make the feedback specific enough that reps could improve on the very next attempt.
A big design risk: if scenario creation feels like filling out a form, adoption will be low. Arena solves this by keeping the AI assistant on the right side, in context, so managers can describe what they need in plain language, then refine it with lightweight controls (tips frequency, mood, voice).
Arena’s strategy leaned into Barge-in: guidance during the moment, while keeping the conversation natural. Design-wise, this forced careful choices around when to interrupt, how “loud” the guidance should be, and how to keep reps in flow.
About
Most sales training breaks down at the worst moment: when a rep gets interrupted, challenged, or pushed into a hard objection. The goal with Arena was to make practice feel like a real call, then make the feedback specific enough that reps could improve on the very next attempt.
A big design risk: if scenario creation feels like filling out a form, adoption will be low. Arena solves this by keeping the AI assistant on the right side, in context, so managers can describe what they need in plain language, then refine it with lightweight controls (tips frequency, mood, voice).
Arena’s strategy leaned into Barge-in: guidance during the moment, while keeping the conversation natural. Design-wise, this forced careful choices around when to interrupt, how “loud” the guidance should be, and how to keep reps in flow.
About
Most sales training breaks down at the worst moment: when a rep gets interrupted, challenged, or pushed into a hard objection. The goal with Arena was to make practice feel like a real call, then make the feedback specific enough that reps could improve on the very next attempt.
A big design risk: if scenario creation feels like filling out a form, adoption will be low. Arena solves this by keeping the AI assistant on the right side, in context, so managers can describe what they need in plain language, then refine it with lightweight controls (tips frequency, mood, voice).
Arena’s strategy leaned into Barge-in: guidance during the moment, while keeping the conversation natural. Design-wise, this forced careful choices around when to interrupt, how “loud” the guidance should be, and how to keep reps in flow.
Practice mode that shows the “climate” of the conversation
The hardest moment in a simulated call is uncertainty. In real life, you read tone, hesitation, and tension. In a simulation, reps can feel blind.
I introduced the thermostat concept: a persistent visual that signals how the conversation is trending, paired with a transcript view so reps can track what happened and adapt in real time.
Practice mode that shows the “climate” of the conversation
The hardest moment in a simulated call is uncertainty. In real life, you read tone, hesitation, and tension. In a simulation, reps can feel blind.
I introduced the thermostat concept: a persistent visual that signals how the conversation is trending, paired with a transcript view so reps can track what happened and adapt in real time.
Practice mode that shows the “climate” of the conversation
The hardest moment in a simulated call is uncertainty. In real life, you read tone, hesitation, and tension. In a simulation, reps can feel blind.
I introduced the thermostat concept: a persistent visual that signals how the conversation is trending, paired with a transcript view so reps can track what happened and adapt in real time.
Results that are specific, comparable, and repeatable
After the call, reps see a results report that separates:
What went well (reinforce strengths)
What needs work (clear gaps)
Skill breakdowns and comparisons (how they stack up vs the org)
A reason to retry (practice loop, not a one-and-done score)
This maps directly to the intended feedback model: transcript with highlights, strengths, mistakes, and suggestions, plus longer-term coaching mechanics like reports and leaderboards.
Results that are specific, comparable, and repeatable
After the call, reps see a results report that separates:
What went well (reinforce strengths)
What needs work (clear gaps)
Skill breakdowns and comparisons (how they stack up vs the org)
A reason to retry (practice loop, not a one-and-done score)
This maps directly to the intended feedback model: transcript with highlights, strengths, mistakes, and suggestions, plus longer-term coaching mechanics like reports and leaderboards.
Results that are specific, comparable, and repeatable
After the call, reps see a results report that separates:
What went well (reinforce strengths)
What needs work (clear gaps)
Skill breakdowns and comparisons (how they stack up vs the org)
A reason to retry (practice loop, not a one-and-done score)
This maps directly to the intended feedback model: transcript with highlights, strengths, mistakes, and suggestions, plus longer-term coaching mechanics like reports and leaderboards.
Other Cases
Other Cases
Other Cases
Diego works smart and fast, communicates clearly, and is a great team player. He’s thoughtful, professional, and brings clarity to complex design problems.
Mindy @Clear Company
Diego is a world-class designer and strong UI advocate. He collaborates seamlessly, sticks to standards, and clearly communicates across stakeholders. His work is top-tier.
Debra @Eskalera
Diego consistently delivered high-quality design work that aligned with Procore’s guidelines and timelines. He brought dedication, skill, and reliable execution to every project.
Karen @Procore
Diego ramped up fast, shipping MVPs within weeks. He’s efficient, creative, and user-centered. Always open to feedback, he brings high value to any design team.
Brian @Alteryx
Diego is a talented UX designer and a pleasure to work with. He approaches his work with a solid understanding of users and tasks and seeks to make experiences clean and simple.
Elizabeth @Alteryx
Diego listens well and delivers design on time with great attention to detail. He is not shy about discussing trade-offs in design choices and is always ready to collaborate on creating user experiences that users find valuable.
Natalie @GroundTruth
Diego adapted fast to our design system and delivered great work on tight timelines. He’s efficient, detail-oriented, and easy to work with.
Liz @Venmo
Diego ramped up fast, shipping MVPs within weeks. He’s efficient, creative, and user-centered. Always open to feedback, he brings high value to any design team.
Brian @Alteryx
Diego works smart and fast, communicates clearly, and is a great team player. He’s thoughtful, professional, and brings clarity to complex design problems.
Mindy @Clear Company
Diego is a world-class designer and strong UI advocate. He collaborates seamlessly, sticks to standards, and clearly communicates across stakeholders. His work is top-tier.
Debra @Eskalera
Diego consistently delivered high-quality design work that aligned with Procore’s guidelines and timelines. He brought dedication, skill, and reliable execution to every project.
Karen @Procore
Diego ramped up fast, shipping MVPs within weeks. He’s efficient, creative, and user-centered. Always open to feedback, he brings high value to any design team.
Brian @Alteryx
Diego is a talented UX designer and a pleasure to work with. He approaches his work with a solid understanding of users and tasks and seeks to make experiences clean and simple.
Elizabeth @Alteryx
Diego listens well and delivers design on time with great attention to detail. He is not shy about discussing trade-offs in design choices and is always ready to collaborate on creating user experiences that users find valuable.
Natalie @GroundTruth
Diego adapted fast to our design system and delivered great work on tight timelines. He’s efficient, detail-oriented, and easy to work with.
Liz @Venmo
Diego ramped up fast, shipping MVPs within weeks. He’s efficient, creative, and user-centered. Always open to feedback, he brings high value to any design team.
Brian @Alteryx
Diego works smart and fast, communicates clearly, and is a great team player. He’s thoughtful, professional, and brings clarity to complex design problems.
Mindy @Clear Company
Diego is a world-class designer and strong UI advocate. He collaborates seamlessly, sticks to standards, and clearly communicates across stakeholders. His work is top-tier.
Debra @Eskalera
Diego consistently delivered high-quality design work that aligned with Procore’s guidelines and timelines. He brought dedication, skill, and reliable execution to every project.
Karen @Procore
Diego ramped up fast, shipping MVPs within weeks. He’s efficient, creative, and user-centered. Always open to feedback, he brings high value to any design team.
Brian @Alteryx