🎺 Rory Sadler

Sales Lead - EMEA

Co-founder & CEO @ trumpet | Collaborative workspaces for revenue teams to centralise buyer journeys | Follow to learn how to increase your sales velocity

How buyers buy has shifted. But most teams are still selling like it’s 2013.

I co-founded trumpet to fix that.

We're helping revenue teams at companies like Gong, HubSpot and Personio make buying easy with digital sales rooms and collaborative workspaces.

We’re helping teams:
• Cut deal cycles by 25%+
• Surface hidden stakeholders
• Create frictionless, personalised buying experiences - from first call to renewal.

As a founder, I share lessons on buyer enablement, GTM, and founder-led sales - the messy, real side of scaling a SaaS business.

If you’re leading a sales org or building a go-to-market motion, follow along.

Member

🎉 We did it! 

1,000+ ⭐️⭐️⭐️⭐️⭐️ reviews on G2! 

Today we’re celebrating a huge milestone as trumpet 🎺 has officially surpassed 1,000 reviews on G2 🚀

Real feedback from real users powering our momentum ✅ 

We're incredibly proud to be the badge holder of #1 Digital Sales Room in the world, alongside:

🏆 #1 Digital Sales Room Globally
🏆 #1 across EMEA, Europe, UK, Asia, APAC
🏆 #1 for SMB, Mid-Market & Enterprise
🏆 #1 Enterprise ROI, Relationships & Implementation - the CS trifecta!
🏆 30+ #1 rankings across DSR, Sales Enablement & Client Portals

The badges are great but the real joy comes from knowing that this is off the back of genuine customer feedback and advocacy.

Thank you to everyone who has reviewed us on G2 and helped shape our journey so far. Your feedback - the good, the insightful, and the constructive - fuels our roadmap and inspires us to build even better 💡

A special shout out to our CS team here at trumpet too, for getting our customers to this point of advocacy - Russell, Maddison, Victoria, Alison, Anna, Louella, Lany Louisse, Bel, Jerwin, Butch - absolute dream team 🙏 

Here’s to the next 1,000! 🥂

Co-Founder & CEO @ trumpet 🎺 | Helping 1,000+ revenue teams win deals through better buyer experiences.

And the band keeps growing 🎺

Following strong and consistent growth in the States, we’re building trumpet’s Customer Success presence and we’re looking for someone who wants real ownership from day one.

You’ll own your own book of customers end to end.
Onboarding. Adoption. Renewals. Expansion. Advocacy.

You’ll work closely with Russell Mitchell - Head of Customer Success, Alison Prator - Founding US CSM and the wider GTM team to help customers get real, measurable outcomes from trumpet and to help us build the CS playbooks we’ll scale with.

You’ll love this role if you:

• Care deeply about customer outcomes, not just activity
• Enjoy commercial conversations and helping customers grow
• Like building process where there isn’t much yet
• Want to help establish a startup’s presence in the US
• Thrive in fast-moving, high-ownership environments

This is early.
There will be ambiguity.
You’ll wear a few hats.

But you’ll also have real influence over how we serve customers, how we retain and expand accounts, and what Customer Success looks at trumpet as we scale.

If that sounds like you and you want to help shape Customer Success at trumpet in the US, apply here 👉 https://lnkd.in/eim5uFBS

Super excited to welcome to two new band members to trumpet 🎺

Big welcome to Shivani who has joined us as Product Manager, and Benjamin has joined as Junior Product Engineer.

Both stood out from the very first interactions.
Not just for their skills, but for their energy, ambition, and the way they consistently went the extra mile throughout the interview and hiring process. 

The kind of candidates who come in curious, prepared, and already thinking about how they can make an impact.

What really got us excited is that they both bring an entrepreneurial mindset with a bias to action, comfort with learning fast, and a genuine hunger to hit the ground running and make their mark. 

Shivani brings a customer-first, high-ownership approach to product, paired with experience navigating demanding environments and complex stakeholder groups. She’s already showing the drive and clarity that will help turn our roadmap into real customer value.

Ben joins with a strong product-engineering mindset and a clear passion for building thoughtfully, learning fast, and working closely with users. His curiosity, work ethic, and ambition made it clear he’ll grow quickly and raise the bar around him.

Finding this level of drive and intent isn’t something we take for granted at trumpet. It’s exactly the mindset we want more of as we continue to build.

We’re incredibly excited to have you both on the journey 🚀

Please join me in giving Shivani and Ben a very warm welcome 🎺

Most people think discovery is about collecting information.

It isn’t.

Real discovery changes how a buyer thinks about their problem.

I was reminded of that recently watching Ali, one of our AEs at trumpet, run a discovery call that ended up becoming one of our top 10 deals to date.

The prospect came in saying they were “exploring digital sales rooms”.

Fairly standard.

A lot of reps would have heard that and jumped straight to features.

Ali didn’t.
He started below the line.

What’s happening today?
Where do things feel messy?
What slows deals down?

The answers were operational.
Long sales cycles.
Too many stakeholders.
Deals slipping because information lived in too many places.

That’s where most discovery stops.

But Ali kept going.

He asked what those delays actually caused.

The tone changed.

They talked about deals dragging on for months.
Stakeholders losing confidence.
Momentum dying late in the cycle.

Then he moved above the line.

What does that mean for the business?

That’s when tangible metrics showed up.

The buyer explained they’d missed revenue targets twice that year.
Several six-figure deals had stalled or died because the process broke down.
Growth had slowed at the exact moment they were preparing for their next investment round.

Now this wasn’t “we want to be more efficient”.

This was “our growth multiple is at risk if we don’t fix this”.

Finally, Ali asked the question most people avoid.

Why now?

The answer was simple.

Doing nothing felt safer.
But it was also costing them real money, real confidence and real credibility internally.

That was the deal.

Not a digital sales room.
Not features.
Not usability.

A clear shift from below-the-line pain to above-the-line priorities, anchored in the buyer’s own numbers by going deep, not wide.

That clarity is what turned interest into action. 

40–60% of B2B deals end in “no decision”, often because the status quo feels safer.

Deep discovery is how you make “doing nothing” the riskiest option in the room.

That’s what effective discovery actually looks like.

“Buyers don’t want to talk to sales anymore.”

Not quite. 
They just don’t want to talk to your sales team the way you’re used to.

Forrester’s latest study on B2B buying behaviour put numbers behind what we’re seeing every day with trumpet customers: buyers aren’t flaky, they’re overloaded.


A few takeaways from the report:

→ 75% of companies say their buying cycle has got longer in the last 24 months

→ The CFO and procurement are now routinely in the deal (76% and 74% more involved)

→ Buyers hit your website, webinars and peer review sites before they’ll even accept a meeting

→ They’d rather get a solid answer now than a “let me get back to you” on another call

→ 80% are more likely to buy when the experience is consultative, not pitchy


If you’re a founder or sales leader, that means a few things:

• Stop hunting for THE decision maker. 
You’re selling to a committee now. Map it, equip it, and give them one shared space to make the decision together.

• Treat your digital footprint as your first sales rep. 
Your buyer has already formed an opinion before your AE opens their mouth.

• Build for the CFO by default. 
Quantify the value, in their language, before they even ask.

• Train reps to run a process with the buyer, not at them. 
Clear next steps, clear stakeholders, clear timeline.

• Arm the team with a deal room that actually helps them answer in the moment: data, proof, customer stories, mutual actions plans, all in one place.


Modern sales isn’t about talking more.

It’s about making project management and making it easy for your buyers to buy.

🇺🇸 And the band keeps growing 🇺🇸


Come join Sean Orlando 🎺 as an Account Executive or Alison Prator as a Customer Success Manager. 

You’ll be one of our first 40 hires.

You’ll work directly with me, our CRO - Ollie Sharpe and our Head of CS - Russell Mitchell to build trumpet’s US presence from the ground up - helping companies create seamless buyer journeys and scaling a best-in-class Sales and CS function.

These are rare roles where you have a genuine opportunity to shape the company’s growth. 

From my experience, this is the most rewarding stage of any startup journey.

But let’s be honest - it’s not easy.

There will be:
• Long hours.
• A ridiculous number of hats.
• A lot of figuring things out solo.
• Regular trips outside your comfort zone.

Startups are hard.
They aren’t for everyone.

But if this sounds like you
• You thrive in ambiguity.
• You’re relentlessly customer-focused.
• You see challenges as opportunities.
• You’re curious, entrepreneurial, and hard-working.
• You value impact over titles.

Then you’ll love it here.

We’re not trying to sell the roles.

We’re trying to find the right people - high-agency operators who want to build something meaningful from the ground up.

If that’s you and you’re ready to spearhead trumpet’s growth in the US, then apply below. 

AE -> https://lnkd.in/epsXk53R

CSM -> https://lnkd.in/eim5uFBS

“Personalising emails takes too long and no one replies anyway.”

I hear this every week.
It’s the wrong diagnosis.

Email isn’t dead.
It’s just been abused. 

Here’s how I think about channels:

Email = nurture + context
Direct mail = underrated + memorable
LinkedIn = show your face + stand out
Face to face = proof you’re not an AI robot
Phone = fastest feedback loop + underutilised

Whatever channel you use, it comes down to HOW you personalise. 

And no, it’s not:
“You went to X university”
or
“You’re the CEO of ACME”

Try these instead.

↳ Talk about people in their team
"Can imagine Lucy and Tim are swamped reviewing CVs..."
Catch their attention by showing you understand their world.

↳ Read job specs for insights
Job specs are cheat sheets.
They’re full of priorities, language and must haves you can mirror back.

↳ BTL selling
Speak to end users first.
Use their language and pain in your note to leadership.
Bellow-the-line selling helps you skip the generic value prop fluff.

↳ Social engagements
Most people don’t post. But they do like and comment.
Use that as a trigger and forward the post with a sharp POV.

↳ Case studies
Look at who they sell to and partner with.
Tailor your message in outcomes their customers already care about.

↳ Types of hires
Don’t just read one role. Zoom out.
A pattern of hires tells you exactly where the business is betting.

Personalisation isn’t a line at the top of an email. 
It’s proof you’ve earned the right to be in their inbox.

How are you creating conversations through all the inbox noise?

Most reps are terrified of disqualifying prospects.
They’d rather chase happy ears for 3 months than ask a direct question. 

But your time is as valuable as theirs.
Every hour spent on hopeful pipeline is an hour lost on real deals.


Quick qualification check:

→ If they can’t articulate the cost of doing nothing, you’re not in a deal

→ If they can’t clearly map out their decision process, it is a conversation, not a project

→ If their questions are all about features, not problems, they’re browsing, not buying


The question I ask to qualify every opp:
“What happens if this problem goes unsolved for another quarter?”

If they shrug or give fluffy answers, you know exactly where you stand.
The best reps I know qualify out more than they qualify in.

Start being someone who challenges how they think about their book of business.

The deals you walk away from are the ones that make the rest of your pipeline move.

Prospect: “Reps are wasting time chasing unqualified deals"

Most sellers: Pain identified and move on 

Best sellers: Implicate pain and go deeper 

They don't just log it in CRM. 

In most deals you’re up against:
• 7–12 stakeholders in the buying group
• Only 5% of the market actively buying right now

Surface-level pain won’t survive that journey.
Implicated pain will.

Here’s the difference.

Surface pain:
“Reps are wasting time chasing unqualified deals.”

Implicated pain:
"If this continues, you’ll miss 18% of revenue target again next quarter, burn another £120k on dead pipeline and best reps will be at risk of leaving."

Same input.
Very different urgency.


What changed?
You did these 3 things on the call:

1. You quantified it
“Roughly how many deals last quarter were lost to no decision?”
“What’s your average ACV?”

2. You broadened the impact
“How does that show up for the board?”
“What does your team feel when they see another deal stall here?”
“If nothing changed by Q4, what breaks first?”

3. You made them aware of the risk of sticking with status quo
“Help me understand, if you don’t fix this, what does next year look like for you personally?”
Let them walk themselves into the implication.


Buyers who see a clear cost of inaction are 2x more likely to move from interested to committed and are 3x more likely to close at full price.

This is why discovery questions lists are mostly useless.
You don’t need 37 clever questions.
You need 5 direct ones and the patience to drill into each answer.

Don’t log the pain.
Make it impossible to ignore.

Fast-return growth and marketing consultant

I founded and lead The Society of Alternative Entrepreneurs; I also own a silversmith business called The Storyhouse of Jewels.

The Society of Alternative Entrepreneurs focuses on practical and lived research into alternative entrepreneurship.

Our community offers guidance and resources to help members leave unfulfilling careers to put their energies, talents and passion towards goals that have personal value to them.

We also share our learning publicly to inspire, comfort and signpost others engaged in or contemplating radical downsizing, emancipatory entrepreneurship or related life changes.

My personal journey saw me quit a career as global head of marketing in the tech industry to embrace makership, creative writing, vanlife, hospitality work and community management.

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🎺 Rory Sadler

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