SaaStr AI London is Dec 1-2!! See You There!!

Helping, founding, funding, and growing B2B start-ups.  Making it a positive-sum game for everyone involved.  VC checks $500k-$4m @ SaaStrFund.com.  2x founder with nine figures of founder exits.

"Do or do not. There is no try."

Specialties: helping people grow and become their best.  Doing not the impossible, but the unlikely.  Never giving up.

Join 10,000 of us IRL at SaastrAnnual.com May 12-14 in SF Bay!!

FREE Weekly Workshops and Live AMAs, Sign up here -> https://www.saastr.com/workshop-wednesday/

SaaStrFund.com investments include:

- Co-led Series A in Salesloft ($2.3B exit)
- Co-led Seed in Pipedrive ($1.5B exit)
- Led Seed in Algolia ($2.3B)
- First VC in Talkdesk ($10B)
- Led Seed in Gorgias ($800m)
- Led Seed in Owner.com ($1B)
- First Investor in RevenueCat ($500m)
- First VC in Logikcull ($280m exit)
- Proud smaller investor in Greenhouse ($800m exit), Sqreen ($400m exit), Automile ($1B SEK exit), Opus Pro, Higgsfield.ai, and many others!
- and much more

Jason M. Lemkin

Possibly the biggest mistakes folks make joining a smaller startup for the first time is this:

You Gotta Know -- It's Not About You

Not trained?
No processes?
Not clear how it works?
Things you disagree with?

Figure It Out.  It's not about you.  It's about the mission.

SaaStr AI 2026 is May 12-14 in SF Bay!! See You There!!

How do founders that have never done it before scale to $10m, $100m, $1B in ARR?

They hire people better than them

This is the mistake most Stretch VPs make. They don’t hire folks better & later more experienced than them as their managers

And they hit a wall at the next stage

1️⃣ Very first month -> 
🔥 72% open rate ->
🚀 Deals already closed from leads that were previously ... ghosted.

I'll join Marc Benioff on Salesforce’s upcoming earnings call TODAY to share how SaaStr Ai deployed Agentforce in just weeks to re-engage 1,000+ missed leads and turn forgotten pipeline into millions of won-closed revenue.

Tune in at 2pm PT: https://lnkd.in/gvNvhynQ

AI reduced SaaStr headcount from 20+ to 3. 

Revenue went from -19% to +47% YoY. 

I'm not telling you to fire your team. 

I'm telling you to be honest about what the next version of your company actually looks like.

"Autonomous agents are here. The guardrail infrastructure isn’t. Every enterprise is about to face this problem: powerful, cheap agents that can do real damage if deployed without security infrastructure." with Harry Stebbings Rory O'Driscoll + me

Meet Harry Stebbings, Jason Lemkin, and Rory O’Driscoll LIVE at SaaStr AI 2026, May 12-14 in SF Bay!! 10,000 of the Best in AI + B2B!! See. You. There

Open article: 20VC x SaaStr: Anthropic Raises $30B, The B2B Software Gravity Well, and Why Corporate America Is Willing AI Into Existence by Jason M. Lemkin • 15 min read

20VC x SaaStr: Anthropic Raises $30B, The B2B Software Gravity Well, and Why Corporate America Is Willing AI Into Existence

We had an AI agent stop ingesting data four months before we noticed. 

No errors. No alerts. 

Just stale outputs wearing the mask of something functional. 

You can't train an AI agent and then just … go away.

Alex Olley

Demandbase Top 25 Sales Leaders 2023 | ABM | Mail Man | Co-Founder | CRO | Personalization Fiend | Ex Lawyer | Cricket and Rugby Nut

I specialise in SaaS technology and using innovative ways to break through to prospects. I believe in treating customers like humans (rather than leads or opportunities) using ABM strategies, Direct Mail, Personalised Gifting and a human element across every touchpoint.

If you want to get in touch with me, send me something...

Co-Founder, Chief Revenue Officer

We started Reachdesk because of a problem we were faced with. Rising above the noise and cutting through the digital clutter is becoming harder given digital channels are exploding. We built Reachdesk to help B2B companies create experiences their customers will love, streamline their existing direct mail and gifting efforts and ultimately help achieve desired results in a busy and competitive world.

This is Natasha - she hit 137% of annual quota last year, closed our first $1m deal and went above her Q4 goal by $130k. We just gave her the "Powerhouse Award" at Reachdesk

She's been with us for 4 years

Tasha learns and gets better every day

Nothing is ever good enough, despite being a consistent top performer

You can't teach that

It's pure mindset

Shoutout to Tasha - you really are a true Reachdesk Powerhouse!

This is Beibei - aka "Slay Slay". She just crushed her ramp goal as a BDR at Reachdesk. She is living proof that outbound is very much alive when many say it's not. Here's what makes her a killer prospector

1. Loves to dial

Record number of diallers

Sits there and does it with energy and enthusiasm every day

Books meetings over the phone

I'm still shocked companies believe this channel is dead

2. Learns fast

The best BDRs are so coachable

They take every loss as a learning opportunity

Small tweaks make a massive difference when they compound

3. Uses gifting strategically

We run gifting campaigns that empower our BDRs

Beibei folds this into her outreach so it makes the prospect feel something

60% of the time it works every time (that's way better than 1% of emails)

Here's to continuing to crush it Beibei

I still remember getting our first 5 Star G2 review and thinking "Holy sh!tballs, we just started a real company". Today we have +1000. Mindblowing

I still remember being told things like:

"You'll get crushed in the US"

"You won't make it past $1m in ARR with gifting"

"The competition are way too far ahead, you'll never catch them"

Well, it's safe to say none of that happened. 

Here's to the next 1000 reviews and many more happy customers!

Ok. Now you have my attention. This was some phenomenal outreach. Here’s why…


1. Research

They found out I was mad on cricket 🏏 They even sent it during the World Cup semi final yesterday 

So they found a way to break through based on something they hat was relevant to me

2. It was hyper personalized 

Cricket bat. With our logo on it. 

It was tied to research and something I would keep

3. The message 

The message was clear. Tied to the research. “Like reviewing every ball in cricket etc we review every interaction”

4. Team selling 

People connected with me messaged me about how a gift was being delivered to our office. 

They surrounded the gift with air cover and a clear follow up 

They even reached out to me team to ensure they were aware this was happening 

This is next level. And it works!

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I stopped reading business books 5 years ago. Most are full of fluffy borderline nonsense. This, however, is different. 

It’s a manual that helps you build better habits

There’s no direction 

It’s all you 

Atomic Habits was one of the better books I’ve read. 

But the workbook, is gold! 

Give it a go!

I’m already sleeping more 

Getting up earlier and plunging every morning 

Eating better 

Seeing more friends 

Spending more time with my family 

Oh, you thought I was doing it to make more money 😂 

The money is only worth it if the important things are taken care of first 🤟

The worst times I've had as a leader were when I lost touch with the people on the front line, had too many initiatives and didn't know my numbers

This is my monthly checklist with the non-negotiables I need to be on top of each month

People, Strategy, Operations

What's on your list that I should add?

Cold water literally saved my life



Ok, maybe a bit dramatic 

But 18 months ago I was in agony. Every day

Couldn’t sleep because of the pain 

Thought it was something way more serious

Jumping in freezing water every day changed this as it was the only thing that helped with the pain

New Lumi cold plunge arrived over the weekend! 

This routine has been a game changer for me 🥶 

6 mins every morning =

1. Better sleep

2. Improved mood

3. Less nerve pain

4. Clearer thinking

I’m not paid by Lumi for this btw

But something that was once a necessity to help manage pain has become a habit that has helped me every day

Give it a go!

The reality of working and having a 4 month old when your partner is ill

Things still need to get done at work (board slides, 1-1s, monthly retros, hiring etc)

And at home (nursery drop off, school pick up, walk the dog, cook etc)

Might be a bit slower than usual today

“You answer cold calls Alex!” 
One of our BDRs said this to me this morning


“Of course I do. Can you imagine me training you on cold calling and never answering calls myself”

Yet we read all over LinkedIn that sales leaders get offended when people cold call them 

Yesterday I answered a call and it was a winner

1. Great pattern interrupt “How have you been Alex?”

2. “I’ve totally called you out of the blue. Can I take 30 seconds to tell you why I called you?”

3. Problem based pitch. Instead of “we help” it was “typically people in your position suffer from this”

4. Open ended Qs “how big of a problem is that for you?”

5. Realised I was the wrong person. Asked for a referral to the right person. I gave it to them

Lesson: calling still works. Just needs to be done well

We are mega focused on this atm. We dropped off a bit last month but bringing this back on track in Feb and March

Still searching around in the dark for ways to break through to people?

Guessing what to send
Hoping it lands
Crossing fingers it feels “personal"

That’s not a strategy. That’s a flashlight with low battery

That’s why Reachdesk turned the lights on with Gifty

Your AI assistant for smarter, revenue-driving gifting

Here’s how Gifty works:
✨ Share who the recipient is and the goal
🔎 Gifty researches them using my inputs and publicly available information
🌍 Next I get gift recommendations aligned to role, region, budget, and objective
🎁 Pulling best-fit options from Reachdesk’s Marketplace and Amazon
💬 And then Gifty drafts a tailored note to spark the conversation

What used to take ages now takes seconds

Less guesswork. More clarity. More conversations.

Want to see how we’re lighting up outreach?
 👉 DM me and I’ll show you

So looks like the Claude partnerships team have been busy. Anyone not got an integration with them or is it just me?

taplio

The Battle

Jason M. Lemkin

Alex Olley

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taplio

The Battle

Jason M. Lemkin

Alex Olley

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jason M. Lemkin's LinkedIn Performance

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Performance ScoreJason M. Lemkin's LinkedIn Performance