Real Stories (and Learnings) from the GTM Trenches Pt.4

Whether you’re gearing up to hide some easter eggs for your kids or glued to the coverage of Augusta, I hope you can take some time to rest/unwind this weekend.


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Before we get you out of your inbox and into the weekend, let’s hear some real world war stories from some of the best revenue leaders to ever do it.

Let’s get into it.

Real Stories (and Learnings) from the GTM Trenches Pt.4





That has become the daily cycle for most knowledge workers – Slack has become an integral part of every day life for just about everybody in tech.

I’d say it’s a necessity now.

But in order to get massive deals across the line, they have to go through all the typical ups and downs like the rest of us.

This week, I asked the infamous Matt Loop, Head of Asia-Pacific at Slack, to open up his war story chest and share some learnings:

“Our top win last year had the full theater of emotions, as is the case with many landmark wins in the sales world. We had to unseat a sticky incumbent (Workplace by Facebook), fend off another corporate standard (the dreaded and horrendous MS Teams) and land a $1m+ ACV New Business deal as the most expensive solution at a time of high budget scrutiny and free solutions available in their portfolio.  

The organization is a large financial institution in Australia, who are focused on becoming the world’s leading digital bank. Given they are coming from a distant 5th place in a country where the “Core 4” banks have ruled for decades, it’s an ambitious goal… but one they’ve been executing well against in the past 5 years. Their adoption of a new core banking platform and excellence in mobile banking are a few ways they’ve started to take market share from the incumbents. 

However, their adoption of internal collaboration tools — namely Teams and Workplace — were not cutting it and we knew that these systems were falling apart and unable to automate their business. 

We sourced this deal through our own efforts and networks within the bank and formally approached them with confidence that we could solve their challenge of collaboration across business units and with their key customers and partners.

After deep discovery and understanding of what the bank was trying to achieve, we went through 9 months of security and solution review. What historically should have taken 3-4 months had blown out amidst macroeconomic uncertainty, heavy business case scrutiny, and expanded decision making criteria and stakeholders. 

However, what remained steadfast throughout was the incredible connection and partnership between a relentless and thoughtful AE and a passionate and innovative CIO and champion….. these two were masters of orchestrating their respective teams and meeting daily to align efforts. 

It was a transparent and trust-tested final few months — and while there were regular changes to our mutual success plan to complete the agreement, the foundational relationship established early and the trust earned throughout the grueling process helped get this over the line.

Happy to say that we are at a GREAT place with this organization.  We’ve surpassed expectations and delivered well ahead of timelines, we’ve got Phase 2+ in scope and weeks away from commencing, and they joined us on stage at our flagship event to tell their story of success. I give much of the credit to the people and teaming on both sides — which is refreshing at a time where all anyone can ever talk about is the death of sales and automation of everything!”

📈 How To Take Action/Learnings:

  1. Signing the deal isn’t winning. While it was great to recognize ACV, see an AE hit her annual quota, hit forecast, and celebrate that milestone, the real win wasn’t until Go Live day when the bank had Slack logos covering the office, the best practices painted onto the walls, and the product got into the users hands. Only at that point had we delivered on our promise.  I recently went to an Obama fireside chat where he discussed that winning the election wasn’t something he celebrated… because he hadn’t actually delivered any value or impact. It was only when the Affordable Care Act was signed that he celebrated….. it was a great reminder to me that the Closed-Won stage of an opportunity is only the beginning.

  2. Face in the Place.  While we all contemplate hybrid work and being productive from anywhere, the time spent on site with the customer getting to know them and their business challenges was irreplaceable. The investment of time drove both personal and professional connection and trust. Despite us being a platform that enables productivity from anywhere and the insane rise of automation in sales, I continue to see customer face time as a consistent factor in our key wins.

  3. Mutual Plan – Mutual Success Plan, Close Plan, whatever you want to call them.  At a time where many companies don’t know how to buy, have process changes, have new people introduced, have stop/start budget and hiring freezes, and variability is at an all time high, having a well designed and mutually agreed series of events to get to a joint goal was hugely critical. It was always in edit mode, but it was our north star that both parties executed against.  I’m finding challenge in most deals where we can’t land this arrangement with a prospect and both parties are “winging it.”

I keep a list of people that I’ve worked directly or indirectly with at past companies that, given the opportunity, I would poach in a heartbeat.

Stephen Farnsworth will forever sit very high atop that list.

We worked closely together in the early years of Outreach, often sharing a tiny hotel room when marketing budgets were a little tight. I’d usually stumble in around 11-12am after entertaining prospects or customers to find him still hammering away on his laptop.

He’s a true professional in every sense of the word. I couldn’t be more excited that we recently convinced him to join one of out portfolio companies to head up their GTM efforts (they are still in stealth but more on them in the future) 💥

Here is a little slice of Farnsy’s story:

“I’ve spent the last ~4 years as a GTM leader. I’ve been able to launch many highly impactful initiatives in that time, often functioning on the team in a product marketer-like role. No matter the role, I’ve learned that people way over-index on the skills directly related to that function. i.e. Product marketers must be master storytellers. Sellers must be amazing at discovery and negotiation. And so on. I’m not sure I fully believe any of those things. Mastery in one skill is certainly useful, but the most effective folks I’ve worked for, with, or worked for me have been able to look forward to their desired outcome, then create & execute a workback plan to achieve it. They’re amazing project managers.

I had the pleasure of working with Max & Scott (sup) at Outreach. A story we too often tell is about Outreach’s 2019 user conference. In a hyper-competitive market, this event was our best opportunity annually to launch products that would ensure our market leading status. ~6 weeks before the conference, product didn’t have anything interesting to announce.

I’d been begging to tell an ecosystem story but didn’t have buy-in or necessary engineering resources. In a month, we built new APIs, coordinated with a dozen ISV partners to build integrations with them, planned a huge joint marketing launch with all of them, and our ecosystem story became the centerfold of our keynote. 

I then joined Workato during a period of insane growth. 200 employees to 800 in less than a year. Crazy revenue growth. One problem – we told a story of enabling everyone to be “citizen integrators.” In reality, virtually all of our users and revenue was from IT. If we continued down that road – simply replacing legacy IPaaS vendors – our ceiling wasn’t particularly high.

I was hired to lead a tiger team focused on creating a market focused on business users, starting with sales & marketing ops. Did that team have any superpowers? I don’t think so.

We just needed to execute the basics, and do so FAST. We launched a persona-based microsite, first call decks, hired subject-matter experts, held exec dinners, etc.

Nothing new – just fast and well planned.

We tripled pipeline in the first quarter. We doubled again in the second. In our first year, we quadrupled our initial revenue goal, then doubled it again in year 2. 

Too many leaders get caught up in the strategy. I’ve always been biased to action and I rarely see that work out poorly.”

📈 How To Take Action/Learnings:

  1. To be a world-class operator, you don’t need to become a master at anything. You need to become an amazing project manager.

  2. Make tight timelines your friend. When your back is against the wall and you have a highly motivated team, you’ll be surprised at what you can pull off. Nothing beats a good forcing function (like a 2500+ person conference!).

  3. When in doubt go back to the basics. Strong Fundamentals + Speed + Bias for Action is usually the winning formula.

👀 More for your eyeballs

  1. This article from 2016 written by the 🐐, Mark Cranney, still rings true today (maybe even more so). In a recent email to me Mark said, “It’s wartime right now, peacetime is over”. When times are tough, every part of your process needs to be tight. Read the article below on “Control of Be Controlled: Sales Forecasting Done Right”.

👂 More for your eardrums

  1. Typically we bring Revenue Leaders and Founders onto the pod but this week we went with someone on the other side of the fence. Tyler Short, General Counsel and Director of Operations at SixThirty Ventures and I talk about how a VC deal can quickly fall to pieces.

  2. Max Altschuler and I catch up on one of our monthly bonus episodes to talk through fund updates, how to host executive experiences (that people actually want to come to), the basics of sizing up an investment, and some reflections from Max’s 36th birthday.

🚀 Start-ups to watch: 

Brendan Short and the Groundswell team just released your new best friend for prospecting.

It gets you a personalized list of top leads with context and an AI-generated email to send with a single click. Groundswell Copilot, powered by OpenAI is their vision for the future of AI-powered prospecting. Integrated right into your existing workflow.

🔥Hottest GTM job of the week: 

Enterprise Customer Success Manager at Seso, more details here.

See more top GTM jobs here

That’s it from me.

Thanks for rocking with us.

If you’re getting value from reading these each week, please share it with a colleague or post your learnings on social.

Enjoy the weekend with your friends and fam.


Thanks for reading The GTM Newsletter! Subscribe for free to receive new posts and support my work.

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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