Simon Jackson

Simon Jackson

@simonjackson.co.uk

Sales Leaders Coach | Author of Stop Managing, Start Leading | Helping you lead with clarity, purpose & a human touch | Book out now #StopManagingStartLeading #TheSalesLeadersCoach #SalesLeadership

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Simon Jackson
@simonjackson.co.uk

An overview of my work with CROs, Sales VPs, and sales leaders – from 1:1 leadership coaching to sales transformation and leadership facilitation.

Simon Jackson
@simonjackson.co.uk

"That feels like micromanaging." Three clients. Same word. Same fear. Same retreat from the very things that make leaders effective. My newsletter unpacks why the label is doing too much work. www.linkedin.com/pulse/feels-... #StopManagingStartLeading #TheSalesLeadersCoach #SalesLeadership

linkedin.com"That Feels Like Micromanaging." Does It?I try to write these newsletters in real time based on conversations I'm having, patterns I'm seeing in clients, things that keep repeating until I can't ignore them. It isn't the most efficient way t...
Simon Jackson
@simonjackson.co.uk

Six months ago today, Stop Managing, Start Leading was published. Grateful for the feedback, reviews, and, most importantly, how people are using it in practice. It’s also been put forward for the Business Book Awards 2026. A small ask:

Simon Jackson
@simonjackson.co.uk

The @thinkers50.com Best New Management Booklist is open for nominations (peer-led, so I can’t nominate it myself). If the book has been useful to you or your team, I’d really appreciate you considering a nomination. thinkers50.com/booklists/ Thank you for the support, it genuinely means a lot.

thinkers50.comThinkers50 Booklists - The Most Influential Management BooksExplore Thinkers50's booklists highlighting the most influential management books, both timeless classics and groundbreaking new releases.
Simon Jackson
@simonjackson.co.uk

A small milestone I’m pleased to share. Stop Managing, Start Leading has been entered into the Business Book Awards 2026. Great to be alongside so many strong titles and authors. If it helps sales leaders build better environments for their teams, it’s doing its job. #BBA2026 #SalesLeadership

Simon Jackson
@simonjackson.co.uk

The average CRO tenure is 18 months. It isn’t a performance problem. It’s a structural one, accountability for revenue without control of the drivers behind it. This week’s newsletter explores why, and what shifts the odds. #SalesLeadership www.linkedin.com/pulse/eighte...

linkedin.comEighteen Months. Is That Really All a CRO Gets?I recently had the pleasure of being a guest on the next + future podcast with Joel and Matt . One of the questions they asked me has stayed with me since.
Simon Jackson
@simonjackson.co.uk

Every role ends. This isn't being pessimistic, it’s just how careers work. The more interesting question is how it ends… and what you leave behind as a leader. I’ve shared a few reflections on that in this week’s newsletter. Over to you once you’ve read it. www.linkedin.com/pulse/your-r...

linkedin.comYour Role Will End. The Question Is: How? | Simon JacksonEvery February, LinkedIn fills up with two very different stories. People delighted to be starting new roles. And others quietly navigating a tough job market. Both are real. And both got me thinki...
Simon Jackson
@simonjackson.co.uk

If you’ve read Stop Managing, Start Leading, I’d genuinely love to hear what resonated, or even what challenged you. Reviews and comments help bring the book to leaders who might benefit from it, so if you’re open to sharing your thoughts, I’d really appreciate it. 🙏

Simon Jackson
@simonjackson.co.uk

A couple of things I saw and heard last week made me stop and think. If AI starts replacing entry-level roles, where do future senior salespeople and leaders actually come from? This isn’t a scare piece. More a reflection, and an open question. www.linkedin.com/pulse/ladder...

linkedin.comThe Ladder Problem: If AI Replaces the Bottom Rung, What Happens Next?I try to write these newsletters in real time, based on conversations I’m having, things I’m seeing in clients, and the quiet patterns that keep repeating. It isn’t the most efficient way of doing it,...
Simon Jackson
@simonjackson.co.uk

Contrary to popular belief, it isn’t always raining in Manchester. Although it was a bit gloomy and wet when I arrived in town this morning (all windswept). Had the privilege of talking at the Supporting Women in Sales event — the first of many inperson events this busy January. Happy New Year!

Simon Jackson
@simonjackson.co.uk

Who’s accountable when things don’t go to plan? I’ve published a new LinkedIn newsletter exploring responsibility, ownership, and accountability, and why accountability shouldn’t feel like a threat, but a natural outcome of good leadership. www.linkedin.com/pulse/troubl... #TheSalesLeadersCoach

linkedin.comThe Trouble Is… There’s No Accountability.I remember a sales leader saying that to me in a moment of real frustration: “The trouble is… there’s just no accountability.” He’d spent a US holiday weekend on the phone with his AVP trying to land ...
Simon Jackson
@simonjackson.co.uk

Who’s really in your corner? I wrote this week about the quiet isolation many sales leaders feel – and why the smartest move isn’t pushing harder, but building the right support around you.

Simon Jackson
@simonjackson.co.uk

It’s a theme I build on in Stop Managing, Start Leading: leaders shouldn’t carry the load alone. Which type of support do you already have, and which one do you need more of right now? #StopManagingStartLeading #SalesLeadership #Resilience

Simon Jackson
@simonjackson.co.uk

I'm thinking of running a monthly sales leadership webinar – live, short, and practical. First one in January. Which topic would you find most useful? Details, and vote for the first topic on LinkedIn 👇 www.linkedin.com/posts/simonj... #StopManagingStartLeading #SalesLeadership

linkedin.com#stopmanagingstartleading #thesalesleaderscoach #salesleadership | Simon JacksonI'm thinking of launching a new monthly webinar series for Sales Leaders – but I’d love your input. I’m planning to run a free 45-minute live webinar at the start of January, as a companion to my boo...
Simon Jackson
@simonjackson.co.uk

I’ve been thinking a lot about the reality of leading sales, especially the parts we rarely discuss. This week’s newsletter explores the personal side: support, isolation, and who we turn to when it counts. Read it here 👉 www.linkedin.com/pulse/who-do... #StopManagingStartLeading #SalesLeadership

linkedin.comWho Do You Turn To When You’re the One in Charge?It’s early December, which means my feed is full of “Top Sales Challenges for 2026”. Most of them say similar things: economic pressure and cautious buyers AI reshaping the way customers research and ...
Simon Jackson
@simonjackson.co.uk

Early’ish start and a coffee at Piccadilly. Edinburgh next. Catching up with a client I normally see on Zoom - and a few others flying in. Finalising January’s Atlanta RKO. Funny how a quick in-person chat can unlock more in 10 minutes than an hour online. #StopManagingStartLeading #SalesLeaders

Simon Jackson
@simonjackson.co.uk

When a team loses its direction, everything starts to wobble. This week’s newsletter is about building a North Star your people can steer by – especially when you’re not in the room. Read it here 👉 www.linkedin.com/pulse/quotas... #StopManagingStartLeading #TheSalesLeadersCoach #SalesLeadership

linkedin.comQuotas Change. Your North Star Shouldn’t.Last week we explored why standards beat expectations, and why clarity beats corporate speak. This week, we move to another pillar of the Vision, Clarity & Culture system.
Simon Jackson
@simonjackson.co.uk

My book Stop Managing, Start Leading was published two months ago today. Thank you to everyone who’s picked up a copy. If you enjoyed it, a short review would really help others discover it too. Grateful for all the support so far. 🙏

Simon Jackson
@simonjackson.co.uk

Most business problems are people problems. That’s why the People System – how you hire and who you hire – shapes everything. This week’s edition: Hire for Attitude. Train for Aptitude. Read it here 👉 www.linkedin.com/pulse/hire-l... #TheSalesLeadersCoach #StopManagingStartLeading

linkedin.comHire Like It Matters (Because It Does): Building the People SystemThe great American philosopher, Homer Simpson, once decreed that alcohol is the cause of, and solution to, all of life’s problems. Tempting as that sounds, I think he’s wrong.
Simon Jackson
@simonjackson.co.uk

If culture really eats strategy for breakfast, why do so few leaders feed it? My latest newsletter explores how intentional culture design separates high-performing teams from the rest. 👉 Read the full piece here: www.linkedin.com/posts/simonj... #StopManagingStartLeading #SalesLeadership

linkedin.comYou Don’t Get the Culture You Want. You Get the One You Build. | Simon JacksonIf culture really eats strategy for breakfast, why do so few leaders spend time feeding it? Most can tell you their strategy, KPIs, and quarterly goals, but struggle to describe what their culture fe...
Simon Jackson
@simonjackson.co.uk

"I really enjoyed reading this book" "Amazing book 📖" "Helpful book" 5-Star reviews all-round on Amazon. But don't just take my Mum, my eldest daughter, and one of my nephew's word for it, check out my book for yourself. Have a great weekend everyone 😄

Simon Jackson
@simonjackson.co.uk

Unashamed plug for my book. Too many leaders still dread their forecast calls - endless prep meetings, more scrutiny, less impact. We don’t need more pressure. We need better leadership. That’s what Stop Managing, Start Leading is all about. #StopManagingStartLeading #SalesLeadership

Simon Jackson
@simonjackson.co.uk

The buzz of launch day has just sunk in… and now comes the bit that matters most. If you do grab a copy of Stop Managing, Start Leading, I’d love to know what you think. Reviews, reflections, or even a quick DM, it all helps and means a lot. #StopManagingStartLeading #SalesLeadership #BookReviews

Simon Jackson reposted

Practical Inspiration Publishing
@practicalinspiration.com

What a month! 😮‍💨 Here are the books we published in the month of September: 'What Next?' by Jane Moffett 'Smart Conflict' by Alice Driscoll and Louise van Haarst 'Stop Managing, Start Leading' by Simon Jackson Incredibly proud to have worked alongside these authors to bring their titles to life!

Simon Jackson
@simonjackson.co.uk

Day one and already #1 Hot New Release in Business & Sales on Amazon. Surreal. 🙏 Thanks to everyone who’s bought so far. If you read it, reviews help more than you know. Kindle’s still just £/$/€0.99 today.

Simon Jackson
@simonjackson.co.uk

Stop Managing, Start Leading lands Sept 30. The book I wish I’d had starting out in sales leadership, 30 years of lessons, wins, mistakes, and coaching conversations distilled into one book. Excited (and a little surreal) that it’s nearly here. #StopManagingStartLeading #SalesLeadership

Simon Jackson
@simonjackson.co.uk

✈️ At Dublin Airport, Guinness in hand, reflecting on a moment from today’s workshop… 🗣️ “Honestly, I don’t agree with any of that. I couldn’t disagree more.” A strong comment—but I welcomed it.

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Simon Jackson
@simonjackson.co.uk

✈️ At Dublin Airport, Guinness in hand, reflecting on a moment from today’s workshop… 🗣️ “Honestly, I don’t agree with any of that. I couldn’t disagree more.” A strong comment—but I welcomed it.

Simon Jackson
@simonjackson.co.uk

At the start of every session, I say: it’s OK to disagree. Leadership and sales aren't black and white. What matters is how we explore the grey. Different views = better thinking. And respectful challenge? It means they’re in.

Simon Jackson
@simonjackson.co.uk

When people go quiet—out of fear or apathy—you don’t get their best. Great leaders create safe environments where disagreement is seen as engagement, not disloyalty. That’s where the real work happens.