Meet Oliver, Your AI-Powered Leadership Mentor

Built for managers in fast-growing organizations, Oliver delivers real-time mentoring to help leaders navigate the challenges of scaling teams — one conversation at a time.

Now in:

Oliver

How's your headspace as you step into the week? Clear? Scattered? Ready?

How Oliver can help you

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🎭 Practice Roleplay for a Tough Conversation

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🗓️Run More Meaningful Team Check-Ins

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💬 Improve the Way You Give Feedback

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📈 Prepare for a Performance Review Cycle

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🌱 Build a Plan for Your Own Growth as a Manager

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⚡ Get Instant Guidance Before a 1:1 Meeting

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🧩 Manage Workload and Delegate More Effectively

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🚀 Boost Team Engagement and Motivation

Grow as a Leader — With Oliver in Your Corner

Everyday Mentoring, One Conversation at a Time

Leadership isn’t a one-off skill. It’s something you build day by day, conversation by conversation. Whether you’re prepping for a tough feedback chat or just trying to get your team in sync, Oliver’s there to guide you, every step of the way.

Why this matters:

The better you lead, the less time you spend firefighting. And the more time you have for what really matters.

Your Leadership Mentor, Where Work Happens

No need to switch apps or dig through a library of resources. Oliver is right there, ready to chat inside the tools you already use. Mentoring shows up where you work. Seamlessly.

What it unlocks:

When mentoring fits into your workflow, it actually happens. No extra effort needed.

The Mentor You Wish You Had (Now You Do)

Let’s be real, leadership can feel lonely. Sometimes you just want someone to bounce things off of, without the pressure. That’s Oliver. No judgment, just practical advice and honest conversations to help you lead with confidence.

How this helps:

Strong leadership skills make you the kind of manager people actually want to work for.

Mentoring for Managers Who Are Figuring It Out as They Go

Most managers don’t get formal leadership training, they’re learning on the fly. Oliver’s here for the moments when you’re thinking, “What do I even say right now?” Quick advice, real talk, and no fluff.

In practice:

Confident leaders build stronger teams, and stronger teams make your life easier.

Leadership Mentoring That Shows Up When You Need It Most

When things get messy — performance reviews, team tension, tricky feedback — Oliver steps in with timely nudges, coaching prompts, and conversation guides to help you handle the tough stuff with confidence.

The upside:

When you grow as a leader, you gain the confidence to handle the tough stuff, and your team trusts you more for it.

Leadership Mentoring That Fits Into Your Day. Not the Other Way Around

We get it: you’re busy. Oliver adapts to your day, offering quick, helpful insights without interrupting your workflow. Whether it’s a 30-second check-in or a deeper conversation, Oliver meets you where you are.

Why it works:

The more you practice leadership skills, the more natural they become — it’s just like working a muscle.

A Leadership Mentor That Works the Way You Do

Whether you’re a planner, a last-minute reactor, or somewhere in between, Oliver flexes with your style. From casual check-ins to structured prompts, it’s mentoring that works with your flow, not against it.

What you gain:

Investing in your leadership growth today sets you up for the opportunities you don’t even see coming yet.

The leadership mentor you didn’t know you needed

Oliver, the AI mentor in Slack

Oliver isn’t just a bot. It’s a conversation-first mentor designed to help you lead with confidence. Built for busy middle managers, Oliver lives inside Slack and offers real-time support on challenges like feedback, delegation, performance reviews, burnout, and team dynamics. All through private, one-on-one conversations.

Easy Setup, Private by Design

Oliver works in DM-only mode. Just like a trusted mentor you message directly.

No @mentions. No listening in on channels.
You can’t add Oliver to group channels or threads.
All messages stay private between you and Oliver.

Once installed, open the Messages tab and say hi. Oliver will respond in a thread below your message, just like a real colleague would.

📖 Read our full Privacy Policy

Personalized Mentoring That Grows With You

When you first install Oliver, you’ll be invited to share a few quick details:

Your role
Current challenges
Skills you want to build

The more you share, the better Oliver can tailor its coaching. This step is optional but it helps personalize your experience fast.

Personalized Mentoring That Grows With You

Practical Guidance, Right When You Need It

Oliver helps you navigate real leadership moments as they happen, and checks in when you need it most.

Here’s how:

Real-time coaching for tough conversations
Proactive nudges that prompt reflection and follow-up
Daily and end-of-day summaries to help you track growth
Roleplay and message drafts to help you prepare
Built-in frameworks for feedback, performance, alignment, and more

All within Slack - no switching tools or tabs.

Practical Guidance, Right When You Need It

Motivation That Feels Good

Oliver keeps leadership growth engaging with lightweight gamification:

Earn badges for streaks, staying active, and the courage to tackle tough topics.
No gimmicks, just a small nudge of momentum and pride

How Oliver Uses AI (and Keeps You in Control)

Oliver uses trusted third-party Large Language Models (LLMs) to generate responses based on your input. Here’s how we do it responsibly:

We don’t share your Slack ID, email, or any identifying info with LLM providers
All prompts are anonymized before processing
Responses are grounded in Oliver’s proprietary leadership knowledge base
Occasionally, content may miss the mark. It’s designed to support your judgment, not replace it.

⚠️ Disclaimer: Oliver’s AI-generated responses may not always be perfect. It’s here to support your thinking — not replace your judgment.

How Oliver Uses AI (and Keeps You in Control)

For HR and Leadership Teams

Help Your Managers Grow — Without Adding to Your Workload

At Oliver, we believe that the best way to grow your business is to grow your people. When managers have a go-to mentor like Oliver, they become more confident, capable leaders — without needing HR to step in every time.

How this helps:

When managers feel equipped to lead handle challenges proactively, they lean less on HR for coaching or conflict mediation.

Scale Leadership Support Without Scaling Your Team

Oliver delivers personalized, in-the-moment mentoring to every manager, so they get the help they need, when they need it, whether HR is available or not.

What this unlocks:

More autonomy for managers. More focus for you.

Equip Managers with Real-Time Guidance

Performance reviews, tough conversations, team alignment? Oliver offers practical advice tailored to your managers’ real situations, so they don’t have to figure it out alone.

Why this matters:

When managers can access advice in the moment, they make better decisions and approach tough conversations with clarity — not hesitation.

Happens Right Where They Work — No Extra Training Required

Oliver lives inside Slack, so managers can reach out anytime. No new tools to learn, no long onboarding process. Just plug, play, and lead better.

The upside:

When leadership mentoring fits into familiar tools like Slack, adoption goes up, and so does impact. No onboarding friction, just immediate value.

Help Your Managers Grow — Without Adding to Your Workload

FAQ

How does Oliver protect my privacy?

While we are aware of your email address, any collected information is used solely to improve app performance, enhance functionality, and diagnose technical issues.
We use Large Language Models (LLMs) to generate responses, but we do not share your email address or user ID with them — everything sent is anonymized and not linked to your identity.
Oliver may collect non-personal data (like logs and device info) to help us improve performance.
We follow industry-standard security measures to protect all collected information.

To learn more read our Privacy Policy

How does Oliver’s AI model get trained?

We’ve worked hard to create a proprietary knowledge base built from the experience of seasoned leadership coaches, trainers, and managers we’ve collaborated with over the years.

Oliver is trained on real-world best practices, Management 101 fundamentals, and practical techniques to help managers confidently navigate everyday challenges — from feedback to performance conversations to team alignment.

Does my company need Slack? What if we use Microsoft Teams?

Right now, Oliver is available exclusively for Slack users.

We’d love to hear if your team uses a different platform, like Microsoft Teams — reach out to us to stay in the loop about future plans!