🎺 Rory Sadler

Sales Lead - EMEA

trumpet

Get deals done quicker with collaborative microsites.

Auto-personalised, interactive & trackable spaces, created in minutes: From cold outreach all the way to onboarding.

Co-Founder & CEO

Pavilion

Executive Member

The User Syndicate

The UK’s first Angel Syndicate and community, designed exclusively for tech professionals.

Our members are UK based and work at the fastest growing companies in the world. They are the end-users of tech and tech-enabled services. Founders can raise money from people that matter and understand their vision. Their users.

We provide high-quality investment opportunities in UK B2B tech start-ups and provide foundational insight into early-stage investing.

We're not a fund. We provide you with access to investment opportunities. You get to choose which companies you do or don't want to invest in!

Angel Investor & Member

Sales Enablement Collective

Member

Hotjar

Learnerbly

Account Executive

Market Minds

Head Of Strategy

Catapult

Head of Sales

Business Development Executive 

HUNT KENDALL CATERING LIMITED

Head of Events

Westminster Entrepreneurial Society

Head of Operations

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

We built trumpet to eradicate long and complex sales cycles. How? With Pods.
Interactive, collaborative and automatically personalised microsites that can be created in seconds. 
Loved by Sales, Customer Success and Marketing teams at over 5,000 companies.

“trumpet 🎺 is the King Of Momentum on G2” 🚀🚀🚀

I think this allows for a humble brag moment 😅

Based on velocity of reviews, the ratings of reviews, interest in our G2 page and web presence as a whole we were #1 Globally for the whole category of Sales Enablement (beating Hubspot and Salesforce, soz guys)

Also #1 Digital Sales Room in the UK 🎺

🎖️ Best ROI and Best Results
🎖️ Easiest to implement
🎖️ 31 badges in G2's Spring 2024 Reports

...Also loving the detailed feedback as we care SO much about our support and ease of use

💬 Ease of implementation - 9.31/10
💬 Ease of setup - 9.19/10
💬 Quality of support - 9.76/10

Huge thanks to all of our incredible customers who have been instrumental in us building a category-leading product that's helping so many companies grow despite these challenging times. 

And of course to our amazing team who work tirelessly to continuously take trumpet to new heights 🚀

Onwards we go 🎺🎺🎺

Customer Success receiving an account from Sales with no context 🙃


An important mindset to have this year for anyone in sales is this: 

The deal does not finish at contract signed. 

It's your job to guide your buyers through the ENTIRE journey seamlessly. 

- Timelines
- Progress updates
- Mutual action plans 
- Intro to Customer Success

These should be introduced as early into the buyer's journey as possible. 

Why?

Because 1 in 4 deals fall through during onboarding.

You're responsible for this part of the buyer's journey too. 

Handover to CS doesn't mean 'no more responsibility' - simple as. 

Effective handovers lead to 

- Higher engagement
- Better adoption
- Less churn 

When was the last time you reviewed your Sales <> CS handover? 

Our team GoodFit.io is growing - would love to hear from you if interested in the Growth Associate role (see below). 

For some context, historically we've has been growing fast through referrals from existing customers, repeat buyers, and through the network of incredible folks our team has met, worked with, and befriended over the years. 

This is awesome. It shows we're working on big problems folks recognise, and that there's confidence (most importantly current and previous customers) we can solve these GTM challenges. 

But we want to grow even faster. 

I feel like I've been saying in podcasts for about 1-2 years "we're just about ready to accelerate growth and expand the team", but I'm glad to say we're finally there.

We decided to hire for a broader Growth Associate role since we're small enough that there's work to do across the customer lifecycle (acquisition, retention, expansion). Uniquely combined with a team of experienced ex-operators, keen to share knowledge with someone curious about the GTM lifecycle end-to-end. (NB. In the short-term the GA will be focused on driving TOFU and customer acquisition). 

In the future the candidate could specialise, remain a generalist, or go on to be a founder themselves. In the short-term I'm sure they'll help make GoodFit a big success, and we can provide an amazing playground for learning along the way. 

Please apply if interested, or share if your network includes individuals this could be interesting for.

The team is absolutely mad, weird, wonderful, talented .... and we're excited for new folks to be a part it ❤️

The days of transactional sales are gone

It's all about consultative selling again 

Whether you're selling 4/5/6/7+ figure contracts 

You can't rely on the same deck and case studies you share with every prospect to close a deal

You need to be going the extra mile to 

+ Thoroughly qualify every opportunity 

+ Stand out from the competition 

+ Create a seamless buying journey that makes saying 'Yes' a no-brainer 


Here's how 

1. Use mutual action plans to create accountability and visibility 

2. Proactively make customer intros as buyers trust third parties 3x more

3. Share micro-demos and interactive demos because no one is watching your hour-long recording 

4. Go beyond ROI and share the cost of inaction, time to implement and time to see results 

5. Centralise everything the buying team needs into one link with a digital sales room

6. Create bespoke business cases to enable your champion to sell when you're not in the room with C-level 

7. Create buyer-facing stakeholder maps with who is involved, what they care about and objections addressed for seamless internal alignment 

What are you doing to win in 2024? 

#BuyerEnablement

Pilots, trials, proof-of-concepts. Are they worth doing? 


It might extend your sales cycle and require more resources

However 75% of companies that engage in a well-structured pilot progress to full implementation.

Pilots aren't just a test run.

They can be the most effective way to convert conversations when run properly. 

Here's how to manage them effectively: 

🎯 Set clear objectives
Know what success looks like for both parties. Without clear goals, you're navigating without a map.

📆 Agree on timelines
Keep everyone focused and accountable. Also, this prevents the pilot from dragging on indefinitely. 

📈 Agreed measurables
Establish KPIs and metrics from the start. This ensures you're measuring progress and success effectively.

👥 Involve key stakeholders
Ensure decision-makers are involved and engaged throughout the pilot. Their buy-in is crucial for moving forward.

✅ Regular check-ins
Schedule periodic updates to discuss progress, address challenges, and adjust strategies with the relevant stakeholders as needed. 

🗣️ Feedback Loop
Encourage honest feedback. It's gold dust for improving your product and you can set up a Slack Connect / Teams channel to manage this.

🏆 Post-pilot review
Book it in from the start to analyse results against your agreed measurables. Use this data to refine your business case and highlight ROI.

➡️ Next steps
Clearly define the transition from pilot to full-scale implementation - ideally, this is communicated as early on as possible, even pre-pilot. Make it easy for the customer to say yes.

Remember, a successful pilot isn't just about proving your product's worth

It's about building a relationship and setting the stage for a long-term partnership.

How are you successfully running pilots? 

Booking meetings is about as hard as it's ever been 😰


Which is why doing your research is more crucial than ever 🔎

But I bet you aren't doing this 👇


Mapping out the potential stakeholders 🗺

We often think of sales as selling to a company. In reality, we're selling to individuals within that company. 

Creating a stakeholder map helps you understand the key players, their roles, and their challenges.

Doing this early on in the conversation increases confidence and trust with your prospects

It also makes for a much warmer convo rather than pitch 


It's super simple to introduce too: 


"Hey Lucy, for our next call do you think it makes sense to bring in Mike and Hannah as we typically see that Marketing want visibility into the set-up of your account?" 


When you know who you’re talking to and their influence on the purchasing process, your conversations become much more strategic. 

Got a discovery call coming up? 

Go and identify the potential buying committee

#BuyerEnablement 

"We're not evaluating any other providers" 



Sounds like a dreamy, plain sailing done deal right? 

Wrong. 

It's a BIG 🚩 🚩 🚩


Any real evaluation will involve 3+ providers. Minimum.  


We're a small company 

But every purchase has to have comparisons 


Next time you're working a deal, invite the elephant into the room and ask 

"Where are you at with evaluating other providers?" 


Being direct will only benefit you and them


➕ Helps qualify conversations 

➕ Saves you time when it reaches sign-off 

➕ Enables you to take control and guide their evaluation


If they haven't looked at anyone

Tell them they're going to be asked to 

Use it as an opp to research for them

Which means less deal risk and allows you to take control of the evaluation 


#BuyerEnablement

How much is being single-threaded is costing you?


$500k a year

With some back-of-a-napkin maths, I calculated the impact of having single-threaded opps on your sales velocity in a year 

Sales velocity is the measurement of how quickly deals move through your pipeline and generate revenue. 

A sales velocity equation uses four metrics 

(Number of Opps x ACV x Win Rate) / Avg Sales Cycle 

It helps to determine how much revenue you can expect to generate over a specific period and top reps track weekly

This example demonstrates the revenue you're missing out on 

And the 10% close rate is being generous too 

UserGems 💎 analysed 500 opportunities and found that a lone wolf (a single-threaded opportunity) has a 5% chance of closing

But take that up to five people (a multi-threaded opportunity), and your chance of winning jumps to 30%

That's a 6x improvement. 

Other benefits of multithreading 

✚ Minimise the risk of employee turnover 

✚ Shorten your sales cycle 

✚ Increase your win rate 

So next time your manager asks if you're multithreaded, you'll now appreciate why 😉

ps - trumpet's digital sales rooms can surface hidden stakeholders to help you get visibility on the full buying committee seamlessly

Messaging is not a one-size-fits-all scenario
 
From outreach to businesses cases, you need to tailor and personalise it to the relevant recipients 

Why? 

Because there are different priorities and pain points at different seniority levels

To break it down 👇 

1️⃣ Managers 
Often focused on the day-to-day operational aspects, they look for solutions that streamline processes and enhance team efficiency. 

For example, when I engage with Sales Managers I'll focus on how trumpet can help their reps follow up with clients faster, use mutual action plans consistently and multithread every opportunity. 

----

2️⃣ Directors
They're strategy-driven and look at the broader impact on their departments. 

The conversation shifts to how our product not only solves immediate problems but also aligns with their long-term goals. 

For example, I'd highlight how trumpet can shorten their sales cycle by 20% - 40% within a certain timeframe or improve forecasting accuracy. 

----

3️⃣ C-Suite Executives
The big picture is their playground. 

They are solely focussed on how a solution affects the company's overall growth and bottom line. 

In these discussions, I'd focus on the strategic benefits of buyer enablement and how prioritising the buyer journey can drive X% in overall revenue growth or significantly enhance market positioning.

----

It all comes down to resonance - connecting the dots between their specific needs and our solution.

Are you tailoring your messaging throughout the sales cycle? 

Selling software is more complex than it's ever been. 

Which is why understanding the web of decision-makers is key. 

Stakeholder mapping is the solution and here's why: 

🔎 Identify Key Players
Know who holds influence as not all decisions are made by C-suite.

📝 Tailored Communication
Each stakeholder has unique concerns. Customise your message to resonate with each of them. 

😌 Streamline the Sales Process
By understanding the hierarchy and decision-making process, you can navigate the sales cycle more efficiently.

🙅🏻 Reduce Friction
Anticipate and address objections from various stakeholders before they arise, smoothing the path to a closed deal.

🤝 Increase Buy-In
Engaging multiple stakeholders increases overall buy-in, making it harder for a single naysayer to veto the decision.

📈 Enhanced Forecast Accuracy
Knowing who's involved and their stance can give you a clearer picture of the deal's health.

🥲 Avoid Last-Minute Surprises
Stakeholder mapping can reveal hidden influencers who might derail your deal if not engaged early.

💪 Long-Term Relationships
Build relationships across the organisation, not just with your primary contact. It's crucial for retention and upselling.

Guess what?

📊 Data Backs This Up

Organisations that perform comprehensive stakeholder mapping enjoy a 15% increase in successful deal closures (Harvard Business Review).

According to CSO Insights, sales reps who engage directly with key stakeholders are 28% more likely to achieve their sales targets.

Stakeholder mapping isn't just a sales tactic.

It's a strategic approach that aligns your selling process with the complex realities of organisational buying behaviour.

You can build stakeholder maps with OrgChart or even Figma and Miro

Soon, with trumpet 🎺 too 👀

Is your Champion really a Champion? Here's 5 ways to test 


There's a lot of talk about spending time on the right opps

And not filling your pipeline with single-threaded conversations with people who said your product is cool 

I've been guilty of this, many times 🙃

But here's how 5 ways to test if your Champion is going to help you make this deal happen

---

📅 Availability and Responsiveness

After every discovery call, I'll tell the prospect I'm putting 15 mins in for us in 3 days. If there's hesitation on their end, it's an early sign they're not invested in this project (yet). 

Truly engaged Champions will make themselves available to you and respond quickly to comms. If they're consistently hard to reach or slow to respond, then they aren't committed. 

--- 

🤝 Make key intros

A strong champion will facilitate introductions to higher-level executives or other key decision-makers. This demonstrates their influence and willingness to advocate on your behalf.

---

🏔️ Objection handling 

The average deal takes 6 months to close and has over 14 stakeholders involved. There's inevitably going to be internal pushback. 

How your Champion handles this and shares these with you is a strong indicator of their influence and commitment.

---

👥 Rally the troops 

Can your Champion persuade other key stakeholders?

Simple one to test, simply by asking them to organise a meeting with other decision-makers. 

---

🏆 Track record 

Have they implemented new solutions or driven change in the company previously? 

A champion with a history of successful initiatives is more likely to be effective. 

---

Keen to hear how you know if your Champion is a Champion? 

We all have that one deal that said they love it 

But they keep pushing the next call back

Or another where we've been a bit too confident with the deal value 

This always comes back to bite you though

Behind the scenes, your manager is looking at your sales velocity 

(# Opps x $ ACV x % Win Rate) / Avg time to close = Sales Velocity 

It measures how efficient and effective you are with your pipeline 

Or simply - how many $ per day you're bringing in 

Top reps know this and that 

- deal slippage
- adding opps that aren't really opps 
- overestimating the contract value 

All heavily impact that number 

A busy pipeline isn't always a good thing so it might be time for a spring clean 😉

Prospecting new joiners - 👍 or 👎? 

It's got to be 👍, especially when it's a senior role. 

They've been brought in to make an impact. 

And they'll have the attention of the wider leadership team. 

With high expectations, they'll be hungry to deliver results, fast.

Meaning it's a perfect time for you to get on their radar and communicate how you can help them win.

Too many people assume new joiners will be busy with onboarding or will take old tooling with them. 

Don't assume - just ask. 

"What led you to book this call? Has X now become a priority or have you seen a change in Y?" 

Avoid this as much as possible

Asking questions with suggested answers can change the way your prospects respond 

It also means they'll address the suggestions rather than the question itself 

Be direct and keep it simple ✌️

The biggest productivity killer? 


Context switching

Hats off to LinkedIn Sales Solutions for recognising this and actioning it with an integration every sales rep has been waiting for. 

✅ Map buying committees
✅ Research accounts
✅ Find the right leads
✅ Be more productive

All within your Salesforce or Microsoft Dynamics 365 CRM 🔥

My only feedback is that HubSpot better be next LinkedIn 😉

What would you want to see next from LinkedIn? For me, it HAS to be an improved inbox 😅

Sales reps "Video prospecting takes too long"

LinkedIn "Hold my beer"

Whilst everyone is busy sending GIFs and voice notes

Why not break through the noise and use LinkedIn's mobile app to send personalised videos easily?

This hidden gem is proven to increase reply rates 

Because who can ignore a personalised hello 😉

Ps - don't go spamming Kyle Asay, but do check out his Sales Introverts training and programs 👌

Taplio

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