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Monica Stewart

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I'm your secret weapon for long-term growth. I've played a key role in facilitating acquisitions for five companies (most notably achieving a 6X growth in valuation in under a year) and have worked with companies like LinkedIn, Trello (acquired by Atlassian), Panjiva (acquired by S&P), redIQ (acquired by Berkadia/Berkshire Hathaway), and Lean Startup. I've sold over $25 million in revenue and contributing to valuations exceeding $200 million. I've had the privilege of addressing hundreds of startup founders and sales leaders globally on sales, leadership, effective communication, account growth, and enterprise sales strategy. You can also find me on podcasts like Sales Leadership and Surf & Sales, talking about sales, negotiation, leadership, change management, account-based sales, account growth, and discovery. Throughout my journey, I've trained and mentored numerous sales professionals and consultants. I've personally sold to over 25% of the Fortune 500 companies including Meta, Target, FedEx, UPS, Maersk Lines, Ralph Lauren, Caterpillar, HBO/Time Warner, Hearst, NASA, and Citibank. My approach extends beyond immediate results; it's about instilling a sustainable, growth-oriented mindset that transforms both leaders and their businesses.

Check out Monica Stewart's verified LinkedIn stats (last 30 days)

Followers
11,713
Posts
9
Engagements
206
Likes
142

What is Monica talking about?

marketingstartup
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Who is engaging with Monica

Stephen Sherry profile picture
Nicole Greene profile picture
Leslie Venetz  profile picture
Muhammad Ziyan Abbas profile picture
Jake Wolpert profile picture
Steven Newman profile picture
Michael Ho profile picture
Charles Moreton profile picture
Dominic Vogel profile picture
Joe Fontana 🐘 profile picture
Kevin Maguire profile picture
 Rabbi Hasan profile picture
Seha Okudan profile picture
Aaron Schaefer profile picture
Chuck Brotman profile picture
Jack Rosenkrantz  profile picture
Meghann Misiak profile picture
Samir Manjure profile picture
Taylor Corr profile picture
Stacie Sussman profile picture
Karim Kuperhause profile picture
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Kyle Asay profile picture
Dean Moothart profile picture
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Rob Snyder profile picture
Jordan Murphy 🧠🦍 profile picture
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Laurie Kenley profile picture
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Cassie Yusofi profile picture
Ashley Healy profile picture
Ethan White profile picture
Jeff Hollihan, MBA profile picture
Matt Stinson profile picture
Hannah Ajikawo profile picture
Steven Conway profile picture
Haris Halkic profile picture
Ryan Howard profile picture
Luke Floyd profile picture
Eric Otten profile picture
Brayden Shell profile picture

Monica Stewart's Best Posts (last 30 days)

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My phone's hottest group chat is called Sales Witches and it's with Leslie Venetz and Meghann Misiak. And now, we're bringing it live to you on Friday. I can't promise you that we'll be sharing ALL the group chat tea on sales, pipeline, LinkedIn gossip and how teams are winning right now....but I can promise you'll leave smarter than you started and have fun :) Join us!

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Leslie Venetz


What happens you combine 3 of the top B2B sales strategiest and a spark of magic? ✨ Sales Alchemy ✨ Join three sales witches (the nice kind) as we gather around the cauldron to discuss what actually drives revenue in B2B sales today. What happens when you stop cobbling together random tactics and start building a strategy that actually works? We’ll explore: 🪄 How to turn fragmented efforts into a focused go-to-market motion 🪄 What the “universal elixir” of sales success really looks like (spoiler: it’s not more tech) 🪄 The magical process of combining insight, action, and alignment to drive pipeline 🪄 And the truths we’ve each uncovered that changed how we sell, lead, and win Every month we'll sit down for an intimate conversation about the most important work you can do to forge stronger connections with your buyers, avoid burnout, earn the attention of enterprise accounts and grow your revenue. Walk away with powerful new energy to incorporate into your sales or leadership practice. No tarot decks required – just three seasoned sales experts ready to share what they’ve learned through years of experimentation, evolution, and yes, a little sales alchemy. 🧪 Come curious. Leave changed.


10

Most deals in your pipeline right now won’t close for this one reason. All of your prospects agree you solve a problem. But they don’t think your product is the best way to solve it. Imagine you're selling an AI SDR tool to a startup founder who needs more revenue. Easy right? Except they're also considering: - Raising prices on existing customers - Launching a new product line to increase ACV - Raising another round before investing more in sales - Focusing on their marketing funnel first - Traditional sales hires Your solution is solving a real problem. But there are 7 other ways of looking at that problem. More deals die not because the prospect didn't believe in the product, but because they didn't believe in the approach. Not every important problem needs to be solved now. Not every important problem needs to be solved by you. The teams I work with don't stop at qualifying for problem awareness. They qualify for solution alignment. How are you doing this today? ————————— 👋 Hi, I'm Monica. I help B2B SaaS founders between $1-$10M ARR create sustainable revenue. ♻️ Share if this could help a founder in your network.


9

The hardest part of growth is letting go of what already works. When I started in SaaS sales, I felt I had to fight to be heard. My strategy was to add value constantly. Take on more. Overachieve. Blow out my numbers. Outwork everyone else. This approach got me to the top of every team. It got me promoted. It worked. Until it didn't. When I moved into leadership, I became that annoying manager who: -Jumped on every call -Dominated one-on-ones -Came prepared with two pages of notes to talk AT my team -Always had an answer instead of a question I thought I was helping but I was actually suffocating their growth. The turning point came when I realized what I needed to do was completely opposite..show up to 1:1s and just sit back. Let my team talk. Help them figure things out for themselves. Create space for them to bring what they needed to be heard. This approach was far more powerful and effective than always trying to do the most. Every belief you'll eventually need to let go of is there because it once served you well. The hard truth is that what got you here won't get you there. Admitting this is not admitting failure, it’s letting yourself evolve. What (currently) successful behavior might be limiting your next level of growth? ————————— 👋 Hi, I'm Monica. I help B2B SaaS founders between $1-$10M ARR create sustainable revenue. ♻️ Share if this could help a founder in your network.


8

People fear two things: change and staying the same. This is what keeps you stuck. It's not your sales process, your team, or the market that's holding you back. It's your beliefs. No one changes their behaviors in a meaningful way unless they first change a belief. But letting go of beliefs that got you this far feels terrifying. Think about it: The founder-led sales process that got you to $3M won't get you to $10M The "always be closing" mentality that made you top rep won't make you a great leader The hands-on approach that built your early team won't scale to 50+ people Deep down you know this. But the beliefs you need to let go of are the very ones that made you successful. I worked with a sales leader who told me: "I'm not sure I'm playing for the winning team anymore." His belief about the company was affecting everything - his energy, his leadership, his results. To change this, we had to examine three levels of belief: - Belief in the mission we're pursuing - Belief that our company does something valuable - Belief in ourselves to connect with and inspire others What belief can let go of to reach your next level?


2

3 things I loved this week: 1. Finding three perfect cafes in Guadalajara 2. That mangos 🥭 and strawberries 🍓 are in season and they are luxuriousss 3. Meghann Misiak inspiring me to try this new post format Have a beautiful weekend!

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10

Same market, funding, talent, but a few big differences: Company A: - Laser focused on their Tier 1 ICP - Knows what to focus on now, 6 months from now, and a year from now - Disqualifies bad-fit prospects within the first call - Everyone gives the same answer when asked about their value prop - Can onboard a new sales hire in less than a month - They're on track to close 3X more this quarter than last. Company B: - Does outreach to "anyone with a CXO title at a big company" - Running 4 different strategies simultaneously, hoping one works - Keeps every opportunity in their pipeline because "you never know!" - Ask 5 people what their product does, get 5 different answers - Believes you need 15+ years of industry experience to sell their product - They have no idea if they'll hit their number this quarter. - The difference is focus, clarity, and the willingness to make hard choices about who they serve and how they operate. P.S. Company A is my client. ————————— 👋 Hi, I'm Monica. I help B2B SaaS founders between $1-$10M ARR create sustainable revenue. ♻️ Share if this could help a founder in your network.


9

There’s something that happens to SaaS startups around $3-5M ARR. You have a compelling vision. You execute relentlessly to get initial traction. You hit milestones. Then you start to plateau. You can see where you need to be in 2-3 years, but your current approach won't get you there. The strategies that worked for $1-3M ARR cannot scale to $10M+. You realize:  - Your sales motion is too founder-dependent - Your team is doing too much and mastering too little  - The CS process that worked for 30 clients breaks at 50+  - The strategy that attracted early adopters is falling flat with bigger prospects The gap between execution and vision cannot be solved by working harder. The founders who break through don't try to stretch their existing strategies. They rebuild their operating system for the next growth phase. The most successful ones understand that being willing to evolve faster than they're forced to is the ultimate competitive advantage. What gaps do you see between where you are and where you want to be? ————————— 👋 Hi, I'm Monica. I help B2B SaaS founders between $1-$10M ARR create sustainable revenue. ♻️ Share if this could help a founder in your network.


45

Tell me you're undercharging and losing deals without telling me... You don't record your sales calls. This hit me hard during a conversation with Scott Sambucci: "If you're scared to record a call because you think a prospect might not like it, despite the fact that it’s a standard practice, how will you ever have the conviction to ask for the sale?" STRAIGHT FACTS. Your industry is not different. Your buyers are not different. Your sales process is not different. There are no "compliance issues" preventing you from recording discovery calls. This is a story you're telling yourself. If you can't confidently ask prospects for this small thing, you've already lost the psychological advantage in the deal. You need to record all your calls and review them obsessively to understand what's working and what's not. Your hesitation to record isn't about compliance. It's about confidence. I will die on this hill 😆 What do you think?


36

Adding more training/playbooks/best practices isn’t working. It’s because your sales team doesn’t lack knowledge. They lack execution. Your team probably already knows what to do (information is free). They're just not doing it consistently. How to close the execution gap: 1. Identify resistance Find who's attached to the current way of working (it might be you). 2. Work through limiting beliefs. It doesn’t matter what worked before, worked at your last company, worked for someone else. 3. Create painful clarity Make your goals unavoidable. Talk about them daily. Make metrics highly visible. The pain of staying the same MUST exceed the pain of changing. 4. Implement radical accountability Create a world where people hold themselves and each other accountable. Define what good looks like. Check progress weekly. Address misses immediately. If getting to where you want to be was simply about knowing what to do, you'd probably already be there. The difference between good and great teams isn't knowledge. It's their ability to execute consistently, even when it's uncomfortable. ————————— 👋 Hi, I'm Monica. I help B2B SaaS founders between $1-$10M ARR create sustainable revenue. ♻️ Share if this could help a founder in your network.


13

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