Don’t Make These 3 Mistakes When Growing a Sales Team…

I’ll be the first to raise my hand and say: I’ve made plenty of mistakes.

Making mistakes is a great way to learn.

In SaaS, we all know the value of failing fast.

The speed of learning is really the key – speed is currency in the startup world.

A solution for speed is to obtain the insight from making mistakes…without actually having to go through the timely process of these missteps.

That’s in GTMfund’s DNA: Insight from world class operators who have been there, done that.

Three overarching learnings from incredible sales leaders who have lived through the ups and downs of growing sales teams at some of the fastest growing SaaS companies is exactly what we’ll dive into today – so you can get the learnings and insight without being in the driver’s seat.

Let’s get into it.


This week’s newsletter is sponsored by Flex.


Avoid These 3 Things

3 pitfalls to avoid when growing and scaling a sales team👇

1) Thinking that more sales headcount = more revenue 

This is a pitfall and simply not true. As Brian Weinberger (SVP of Global Sales at Sisense) expresses, this thinking is like taking an old model and applying it to a new software company. In reality, success hinges on providing robust pipeline support to Account Executives (AEs).

Avoid premature AE expansion. 

Waylon McGill (Partnerships Manager at SaaStr) warns that adding headcount before AEs have better attainment numbers can actually lower revenue because you will be taking leads away from more experienced, better reps to give them to new reps with lower win-rates. 

Sean Marshall (ex-SVP of of Global Sales at Klaviyo) has implemented measures to avoid unnecessarily scaling sales headcount, always considering the question: “Can we get a little bit more out of the team that we have before we go hire another human?”. You can hear more about his playbook and experience running efficient high performing sales teams at Klaviyo and other companies in The GTM Podcast Episode 68

2) Trying to grow outbound without marketing support

Growing outbound without marketing support is like trying to play a symphony with only half the orchestra. Without synced collaboration, the melody of outbound efforts may fall flat, missing the full spectrum of notes needed for a truly epic performance.

To illustrate the importance of synchronization, David Stillman (Founder at Stori) evangelizes the importance of ensuring that everything is in sync – not just outbound cadences, rather everything from website, to first call deck, to talk track, etc. 

Whether finding your sweet spot in the market by leaning into product marketing or increasing outbound effectiveness by running proper ABM strategic campaigns – outbound and marketing should be working in lockstep together. 

Trying to grow outbound without marketing support comes at a cost. Waylon McGill warns: “Unless you have incredible win rates and strong ACV it’s an expensive way to grow revenue.”

3) Overlooking the importance of operations

Putting the right systems and processes in place makes it easier, as Brian Weinberger advises. 

A well oiled operating system can more greatly adhere to the constantly sought after ‘set it and forget it’ state. It becomes the unsung hero working tirelessly in the background to help you win. 

For example, Florin Tatulea (Director of Sales at Barley) advises against letting all 10+ BDRs have their own sequences and email templates, as it makes it more difficult to coordinate and test what is working. Rather, sticking to 4-6 sequences across the team (exact numbers may vary based on team size) and empowering BDRs to focus on the context and personalization of the email templates will allow for smoother operations and better measurement for optimization. 

As another example, Brian Weinberger emphasizes the importance of having a really clear and clean qualification process for meeting to qualified pipeline. Everyone should be clear on how the team wins. 

If operational processes aren’t tight, neither is the pipeline.  


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🍿 Upcoming Live Digital Event:

GTMnow’s inaugural live digital event is coming up in less than 2 weeks! Led by Lars Nilsson, who coined the phrase account-based sales development himself, this will be both a strategic and tactical session.

Save Your Seat


👀 More for your eyeballs:

Interesting article that discusses Retrieval-Augmented Generation (RAG), emphasizing its significance in enterprise AI. RAG combines the capabilities of both generative and retrieval-based models, enhancing natural language understanding and enabling more effective information retrieval. Check out the full article linked in the image below.


👀👀 More for your eyeballs:

We recently partnered with Blueprint & Accelerate HC to help companies get all the support necessary for hiring. From entry to executive roles, from strategic planning to active hiring – GTMfund’s talent partners have you covered for all GTM hiring needs. If you’re curious or are actively hiring, you can learn more here.


👂 More for your eardrums:

Sean Marshall most recently spent 4.5 years as SVP, Global Sales at Klaviyo. He helped scale the sales organization from 15 to 300 people, while growing annual recurring revenue from $25m to over $450m. Tune in to find out all of Sean’s best sales strategies!


🚀 Start-ups to watch: 

OfferFit announced their $25M Series B funding this week!
OfferFit’s Automated Experimentation Platform is the fastest, most scalable way to accelerate testing and learning. Full link in the imagebelow👇


🔥 Hottest GTM jobs of the week:

Product Marketing Manager & Partnerships at Crossbeam – more details here.

Sr RevOps Manager at Amper – more details here.

Solutions Architect / Customer Success Manager at Closefactor – more details here.

See more top GTM jobs here


That’s it, that’s all.

For now, that is! Insight around growing sales teams has been a highly requested topic. If you would like us to do an even deeper dive into the subject, let me know in the comments.

Is everyone getting ready for the upcoming holiday? Prepping turkeys?

We just wrapped up a fantastic week in London and Dublin, where we hosted a dinner for 40 GTM executives and participated in a GTM event as the keynote speaker and a panelist. I know I’m a week early…but feeling extra thankful.

Have a great weekend ahead!

Barker ✌️

Please support our sponsor so we can keep providing you with great content for free: Flex.
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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