Peter Ahn

I just got absolutely GRILLED by 100+ founders at Southpark Commons and honestly... it was awesome!

I do a lot of coaching calls, but there's something different about being put on the spot in front of a room full of founders who are ALL dealing with the same stuff you probably are right now.

These weren't softball questions either.

We're talking:
"Peter, how the hell do I sell enterprise when I literally have zero logos and no SOC 2?"
"Should I bring up competitors or am I just shooting myself in the foot?"
"What do I do when someone asks me to build a feature but they're clearly not the decision maker?"

I definitely said some things that might sound counterintuitive (like why you should tell prospects you have no enterprise customers), but that's because most of the "conventional wisdom" about sales is honestly pretty terrible for early-stage founders.

I'm thinking through answers in real time, and there are definitely moments where I'm like "wait, let me think about that differently..."

If you're a founder in sales, this is probably the most honest conversation about enterprise sales you'll hear this week.

#foundersales #startupsales #salescoaching #enterprisesales #b2bsales #southparkcommons #salesstrategy #salesmindset #salesquestions #startupadvice

5 months ago | [YT] | 0

Peter Ahn

A month ago, I live-negotiated against a bot — and honestly, it was nerve-wracking.
(Yes, even as a sales coach.)

Today, I’m excited to finally share that bot with you.

✨ The backstory:

When I first tested Hyperbound's sales bot, I was blown away by how realistic it felt ( 👏 Sriharsha Guduguntla, Atul Raghunathan)

It immediately sparked an idea:

What if my clients could practice tough sales conversations with AI anytime, not just during our live sessions?

So I built a bot that acts like a head of procurement, pushing back on your pricing proposal after a successful POC.

(Special thanks to my advisees Howard Zuo and Arthur Wu at Dataland for inspiring this scenario — check them out if you want to see how best-in-class AI customer support agents can transform your operations)

🔗 If you want to try the negotiation bot I built for startup founders and sellers, check the comments section for the link to try it out

❓How will you score against the bot? Comment your score below!

6 months ago | [YT] | 1

Peter Ahn

I love impacting founders at the earliest stages of startup ideation while giving back to my local community here in San Diego.

Last week I had the pleasure of engaging with bright high school entrepreneurs who are bold and bravely exploring their own startup journeys.

Over the course of three days, my friend Howard C. and his team mentor these high schoolers through the High School Small Business Academy at the California State University San Marcos Innovation Hub.

On the last day as they prepared for their final pitches, I spoke to the group about my journey and what it means to stand out authentically in a crowded market.

I was impressed by the engagement from the group and came away inspired by the genuine passion for startups and their fresh perspectives on the world.

During my talk I focused on three things I’ve found to be critical to success across the founders I’ve coached:

🧠 Founder vision
→ Buyers bet on founders and their way of thinking.
→ The most successful founders I’ve met and coached have a clear vision that goes beyond their product and that builds opinionated trust with their prospects.

🔎 A clear solution for pain
→ Without a burning pain point, it’s hard to justify budget.
→ The best founders can clearly identify and articulate pains and quantify them when showcasing their product.

💻 One of one technology
→ The most visionary founders can take early stage technical decisions and turn them into compelling stories around why their technical backbone out competes anything else.
→ What may seem like too “in the weeds” in terms of your technical architecture can have big implications for building your technical moat while educating buyers on your superpowers.
→ Successful founders can zoom in and out of these technical details to build a compelling story when on the surface many products look similar.

Thank you Howard for having me at the Innovation Hub and grateful to all the energy you’re putting into molding the next generation of our leaders.

Do you remember what it was like to be in high school and what business ideas did you have back then? :)

Skip the Carousel

1 2 3 4

6 months ago | [YT] | 6

Peter Ahn

🎬 I'm thrilled that the full conversation of me interviewing Hyperbound cofounders Sriharsha Guduguntla and Atul Raghunathan is now live!

In a sea of platforms focusing on prospecting and demand generation, Hyperbound stood out to me as one of the few that is focusing on the actual live craft of selling.

While generating quality leads is a must-have for companies, in such a noisy world how a seller shows-up from first call to close can sink or accelerate a deal.

It's why I was blown away by Sriharsha and Atul's vision to democratize sales practice across small and large teams through intentional, AI-driven practice scenarios.

With their various prospect voice bots, sellers can now hone their phraseology while drawing inspiration from recorded practice sessions across their leaders and peers.

Beyond talking about Hyperbound, we also dove into topics like:
🎙️ Why it's so hard to stand out within the AI sales tech space
🎙️ Founder-led sales challenges and how Sriharsha and Atul navigated them
🎙️ The state of diversity within tech sales

Check out the full interivew and yes, my practice negotiation with the Hyperbound bot is still coming 😃

6 months ago (edited) | [YT] | 1

Peter Ahn

"It just works"

I heard this phrase repeatedly when I was selling Dropbox to businesses.

To many end users, Dropbox felt magical because files could be shared seamlessly across whatever device and environment you were in.

Back in ~2013 this smooth file sharing experience surprisingly wasn't the norm across other platforms.

But what was even more powerful during enterprise sales discussions was going a level deeper to explore why under the hood, Dropbox's sync engine was so reliable.


And although we didn't have all of the enterprise features that Microsoft and Box were touting during their pitches, the key, early architectural decisions Dropbox cofounders Drew and Arash made would be the difference in many of my enterprise deals.

That decision was to design the sync engine in a way that still worked whether or not you had consistent internet connection.

Because files were synced in smaller chunks, you could lose internet connection halfway through the upload and the rest would get up to the cloud whenever you regained internet connection.

→ So while we didn't have encryption key management, Dropbox's delta sync technology ensured critical files were there.

→ While we didn't have password protected links initially, Dropbox end users could rely on files getting to their final destination.

→ While we didn't have certain DLP (data loss prevention) capabilities, 𝘋𝘳𝘰𝘱𝘣𝘰𝘹 𝘫𝘶𝘴𝘵 𝘸𝘰𝘳𝘬𝘦𝘥.

It's sometimes crazy to think that one architectural decisions had such a big impact on large enterprise customers taking a bet on us, but it did.

𝗔𝗻𝗱 𝗶𝘁'𝘀 𝘄𝗵𝘆 𝘄𝗵𝗲𝗻 𝗜 𝗰𝗼𝗮𝗰𝗵 𝘀𝘁𝗮𝗿𝘁𝘂𝗽 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝘁𝗼𝗱𝗮𝘆, 𝗜 𝘂𝗿𝗴𝗲 𝘁𝗵𝗲𝗺 𝘁𝗼 𝘀𝗶𝗺𝗽𝗹𝗶𝗳𝘆 𝘄𝗵𝗮𝘁 𝘁𝗿𝘂𝗹𝘆 𝗶𝘀 𝘁𝗵𝗲𝗶𝗿 𝘁𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗺𝗼𝗮𝘁 𝗮𝗻𝗱 𝘁𝗼 𝗲𝗻𝘀𝘂𝗿𝗲 𝗯𝗼𝘁𝗵 𝘁𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗮𝗻𝗱 𝗻𝗼𝗻-𝘁𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗯𝘂𝘆𝗲𝗿𝘀 𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱 𝘁𝗵𝗲 𝗽𝗼𝘄𝗲𝗿 𝗼𝗳 𝘁𝗵𝗼𝘀𝗲 𝗲𝗮𝗿𝗹𝘆 𝗮𝗿𝗰𝗵𝗶𝘁𝗲𝗰𝘁𝘂𝗿𝗮𝗹 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀.

If those technical decisions are addressing a core, burning problem, it can help you become a strategic vendor even if you're being fed that "you're not enterprise ready".

Take a listen to the full video where I break down how critical Dropbox's delta sync technology was for my deals.

What technical moat are you building for your startup and are you surfacing it enough during your pitch?

7 months ago | [YT] | 0

Peter Ahn

Sometimes a good old fashioned chat with someone on a similar journey to you can unlock inspired creativity.

About a year ago Monica Stewart invited me to a LinkedIn emotional support group.


It's been such a huge help to someone like me figuring out how to navigate showing-up authentically and consistently on this platform.



Folks like Monica, Leslie Venetz and Meghann Misiak are the most active in the group and are extremely generous with their advice, thoughts, and support.


And recently over a virtual coffee chat with Meghann, she listened to my passion for workshopping authentic sales phraseology and suggested I noodle on launching a YouTube series called, "Say this not that".

I loved the idea so much that after our chat I recorded 7 mini episodes designed to help founders and sellers rethink how to say what might otherwise be seen as mundane and robotic sales language.


How you say what you want to say is critical to building buyer trust, especially today.

I hope that with this series sellers can gain some perspective on how they can elevate their own authentic sales voice without following or conforming to an old school script.

I'll be uploading the first few episodes over the next week so be sure to turn on post notifications and subscribe for updates!


Who is someone who as recently helped unlock creativity for you?

7 months ago | [YT] | 2

Peter Ahn

Getting great at sales takes practice.

It's why I used to obsessively hone my phraseology in front of a mirror earlier in my career.

I wanted to make sure I showed up polished and with presence.

I turned my insecurity of being an Asian-American seller into motivation to show-up prepared with more practice under my belt than any other rep.

Hyperbound is now unlocking that practice for the modern sales rep at a scale that wasn't possible before AI.

And last week I had a blast interviewing its two brilliant, yet humble, cofounders Sriharsha Guduguntla and Atul Raghunathan.

In creating Hyperbound, they've radically increased access to practice for sellers and founders looking to hone their sales craft while finding their authentic voice.

Sellers can now use Hyperbound's AI voice bots to practice their cold call, discovery, and negotiation skills whenever and wherever they want.

It was an honor to spend time with them as we discussed their vision for enabling both small and large sales teams to get on message and on brand faster than was ever possible.

In our interview, beyond Hyperbound, we also discuss:
→ Why it's hard to stand out as an AI platform targeting GTM
→ The challenges and rewards of navigating founder-led sales
→ The state of diversity within tech sales
→ Other AI platforms they are keeping an eye on

At the end of the interview, I even jumped into their AI practice environment and engaged with a negotiation bot I've been excited to share with my founder community!

I have to admit, I was nervous to do the practice live, but it underscored the importance of having something like Hyperbound to keep my skills fresh as a coach :)

Subscribe for the full interview launching soon on my channel!

How often are you practicing your sales skills?

Skip the Carousel

1 2 3 4 5

7 months ago (edited) | [YT] | 6