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

The one hire I don't need, and none of my portfolio cos need, is a "Strategist"

I know at certain stage in many folks' career, that's what they want to do

Advise on strategy more than do work themselves

No criticism

But most startups only need a few hours of this at a time

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

My #1 piece of advice for GTM leaders in January 2026: Deploy an AI agent yourself.  Now.  This month.  Don't hire an agency. Don't tell someone on your team to do it.  Do it yourself.  Roll up those sleeves again. 

Deploy an AI agent into production, for real, yourself. with Lenny Rachitsky

And for junior sales & GTM folks? Embrace it. Be the one that embraces every bit of output from AI Agents.

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 bad. I wanted pricing from a company to compare them to what we are currently paying. I won't name them, but let's call them "Can'treach"

Step 1: go to pricing page (not even an estimate on pricing on it)
Step 2: fill out form to request pricing
Step 3: form gets way longer and actually requires ~8 steps to complete
Step 10: confirmation message saying "We will email you pricing"
Step 11: get called by an SDR trying to qualify me
Step 12: I wrote this LinkedIn post because I'm so angry about how hard it is to just get a ballpark price / some level of customer centric approach to buying. I won't give them my time as they've already eaten it up

Apparently 85% of the sales process is complete before we even speak to a sales person. This one is 100% complete before I even got there....

Is anyone else struggling to get basic info from providers?

“One day I will be the Top AE at Reachdesk”



I remember this is what Siôn said to me on Day 1

I’d heard it 100 times before from other AEs

Within a month I could see he meant business

He’s consistently been top of the leaderboard for years. Always being the one everyone wants to beat (in a healthy way)

Last night Ben and I celebrated with Siôn at Sushi Samba

Here’s to you Siôn-ie

You’re a closing machine

No alternative text description for this image

We would have died like many of our competitors if we had removed our Outbound team

BDRs will never be removed from Reachdesk

While many companies eliminated this function, we did the opposite. 

We invested in it

Our Outbound win rate this quarter is 31%

It’s bringing in real dollar 💵 

It’s our pride and joy - the lifeblood of the business 

And we use gifting / direct mail as part of our outreach. So no surprise it crushes it for us as we have a secret weapon to cut through the noise 

Some say we literally “drink our own champagne”

I’m hiring world class BDRs in NYC and London

Tag anyone you think is top 1% or DM me if you think you are

The worst investment b2b marketers make is events. Specifically trade shows/conferences. That's why we are doubling down on them because we have an edge

I've attended +200 events in my time

95% of the experiences are garbage - they lack human connection and experience. 

The playbook usually goes something like this:

1. Spend $50k on a booth
2. Fill it with crappy swag nobody wants
3. Send a team of 5-10 reps to loiter and prey on passers by
4. Scan attendees' badges
5. Send automated email asking to book a meeting
6. Tick the MQL box and gamify the system

Nobody wants this. It's a terrible experience, waste of money and little turns into revenue

Our playbook is something like this:
1. Sponsor events that match ICP - ask for prior year sample attendee lists first
2. Datamine lists and search LinkedIn for people attending the event
3. Partner with another company to host a side event / activation (sometimes get a booth for a large event we know works)
4. Co-invite prospects based on ICP and Persona fit - ask for referrals directly to right personas if not attending but their colleague is
5. Send Spa Voucher in advance using Reachdesk - "Events are hard. Here's something on us to enjoy after the event". This is part of the message when you arrange to meet
6. Meet in person at the event with clear location sent prior
7. Send gift to thank them for their time

This sees 50-60% response rates pre-event and attendance is nearly 100%

It's all targeted at ideal customers and personas so conversion to pipeline is also high

We aim to have at least 10 pre-booked meetings before we head to the event

What do you think?

I'm looking for world class BDRs in New York and London. 50% of our pipeline comes from Outbound - this isn't new to us! We've been doing it since day 1. DM me if you deem yourself to be in the Top 1% and looking to push on with your career in Sales...

2020 - having kids really gets in the way of life 
2026 - I’m never going to get this time back with my kids. Savour every moment 

I have 3 kids (6, 3 and 0.3) and used to battle this mental game with myself on how to do my job and enjoy being a father 

I was always losing as work came first 

A mentor told me “if you want to succeed you have to go all in on one thing.” Worst advice I ever got 

Then a fried once said to me “Enjoy every moment, before you know it they’ve left home. You will never get that time back”

The game changed 

I transformed my life so I could enjoy every moment with my kids

Time blocks 
Leaving my phone in another room
Working early
Working late 
Keeping weekend clear
Giving up my Quins season ticket (sob)

I even took my son shopping with me - something I would have avoided at all costs years ago 

Sometimes you can’t go all in

It doesn’t mean you will fail

If you interview a leader and they say “I did that” and they never give credit to their team, don’t hire them

Leaders shouldn’t take credit for hitting targets. Their team should

Leaders don’t do all the heavy lifting. Their team does most of it. 

Leaders shouldn’t be coming up with all the good ideas. They should be getting most of them from their team. 

The best ideas, the greatest successes, the big wins - your team did that. 

Not you

Every end of quarter we used to try to close a ton of deals on the final day. We called it the boiler room. It was a sign of failure. 

Every seller would be in the room trying to get deals done. 

We’d close a load on the final day

But it was rarely enough to hit target 🎯 

Don’t get me wrong, you should try and close as much as possible. End of quarter magic happens. 

But if most of your revenue comes in at the end of the Q, you ain’t managing that pipeline well.



The reality is, buyers will change behaviour and timelines if they have a carrot 🥕 

So incentives work

But this doesn’t work half as well as understanding the cost of inaction and missing timelines on th customer side 

We now build mutual launch plans that visualise the future state and when they will see value

We also show the cost of delaying and make sure we can algin timelines to theirninternal process

Once you nail thag, you close deals in a timely manner that makes sense for the customer 

We still do boiler room. But to be honest that stress and energy is no longer there. We hit every quarter early last year. 

Boiler room has turned into an end of Q celebration 🎉

Money definitely buys happiness

Discuss...

taplio

The Battle

Jason M. Lemkin

Alex Olley

Followers

Posts

Engagements

Likes

Performance ScoreJason M. Lemkin's LinkedIn Performance

Performance ScoreAlex Olley's LinkedIn Performance

Ready to grow your LinkedIn presence?

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

Performance ScoreAlex Olley's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreJason M. Lemkin's LinkedIn Performance