MSP Consulting

❝ The best way to make a dream come true is to wake up.❞
― Anna Wintour

For over 10 years, I built and grew exceptional sales teams that propelled companies to acquisition. 

Then, in more ways than one, I decided to take Anna Wintour's advice. I abandoned the day-to-day grind of operations so I could impact exceptional leaders at special companies in ways that mattered.

At MSP, I help founders and sales teams reach their goals in the fastest way possible. In every case, we begin with the most impactful priority and advance from there. I’ve helped dozens of companies unlock their next level of growth, delivering well over $20M in revenue and $100M in value creation.

Founder

Pavilion

Pavillion is a private community of sales and marketing executives.

Executive Member | CRO School Graduate

Customer Success Collective

Member

Uprise - Embedded Financial Advisory

Advisor

Happy Wellness Consulting, Inc.

Happy Wellness brings 40+ years combined of Wall Street & Startup experience to help wellness-related founders with fundraising and strategy. Our core focus is on Pre-Seed to Series B, within the food/beverage/CPG/mental health/fitness/nutrition/healthcare markets. Our expert team of 10+ professionals help founders with sales strategy, fundraising, go-to-market, revenue growth, product development, ops & branding.

Additionally, we support a large venture ecosystem of investors (Angels, VCs, Family Offices) and strategic partners by brokering relationships and helping institutional funds raise capital.

Altru

❝ Price is what you pay. Value is what you get.❞ 
          ― Dr. Robert Anthony

✪ Highlights:
    ‣ 5X increase in ACV
    ‣ Successful acquisition at 6X starting valuation in under a year.

I was brought in by Altru’s CEO and VP of Client Strategy with one mission in mind: to get acquired. 

Though the team was capable, their contracts were underpriced, and the perceived value of their product was lacking. To jumpstart growth, we needed to rethink the entire sales process and go deeper with our best clients. 

We turned tiny subscriptions with enterprise companies into true enterprise relationships, and by the time Altru was acquired, the client strategy team had become an unstoppable enterprise growth engine.

VP, Client Strategy 

Skaled

❝ Enthusiasm is common. Endurance is rare.❞ 
          ―  Angela Duckworth

✪ Highlights:
 ‣ 40% increase in revenue from existing clients
 ‣ Built account management function from the ground up
 ‣ Led sales trainings for VCs, accelerators and LinkedIn Sales and Marketing teams

At Skaled, a modern, technology-forward sales-consulting firm, I was recruited as the third musketeer of their executive leadership team, beginning in operations before heading their consulting practice.

I led client strategy across four practice areas and was responsible for retaining and growing the entire existing client portfolio. In doing so, I delivered transformative increases in revenue and efficiency.

Principal 

redIQ

❝ The moment you doubt whether you can fly, you cease for ever to be able to do it.❞
― J.M. Barrie

✪ Highlights:
 ‣ Acquired by Berkadia/Berkshire Hathaway
 ‣ Grew Team by 300%
 ‣ Increased Revenue by 600%

My goal at redIQ was to build a profitable sales org in a highly competitive market. 

More than anything, our team needed confidence. Along with leading a massive shift in mindset, we re-engineered our sales process - resulting in expanded pipeline, higher conversion rates, and dramatically higher contract values.

I grew the team from 2 to 15, and was responsible for $6.5M in revenue. 

Our growth in sales was integral to redIQ's acquisition at 3X our starting valuation, and 80% of the team I hired is still there today.

Chief Revenue Officer (CRO)

Trello (acq Atlassian)

❝ Opportunities are usually disguised as hard work, so most people don't recognize them.❞ 
― Ann Landers

✪ Highlights:
‣ Trello acquired by Atlassian
‣ Sold to NASA, Hearst, Boeing, JPL

I was Trello evangelist long before joining their team, but even I used the free version of the platform.

So, when I was asked to mentor their team, sell to existing clients, and lead enterprise sales initiatives, I knew we had our work cut out for us. 

It was a journey, but a rewarding one. In bringing on clients like NASA, Hearst Publications, Caterpillar, Boeing, and JPL, we laid the groundwork for Trello's acquisition by Atlassian, and many of those I mentored are leaders of Trello today.

Director, Strategic Account Sales

S&P Global Market Intelligence, Research Division

❝ Find out what you like doing best, and get someone to pay you for doing it.❞ 
— Katharine Whitehorn

✪ Highlights:
‣ Panjiva acquired by S&P
‣ Grew sales team from 4 to 50 employees
‣ Led pivot to Enterprise sales
‣ Closed largest deal in company history 

After noticing significant trends in accounts and client feedback, I proposed a strategic pivot towards launching and implementing of new data analysis SaaS product with a focus on finance, consulting, and logistics sectors. 

As the link between our sales and product/engineering teams, I came to understand the meaning of relationship capital, gaining extensive experience in leading between departments and disciplines.

Director, Enterprise Sales

As the 4th sales hire, I was a core member of the Panjiva (now S&P Global Market Intelligence) GTM team. 

I refined our market positioning and GTM strategy while skyrocketing average contract values. 

Along with all sales and product-related training and development, I was an instrumental part of the leadership team.

Senior Account Executive

Founder @MSP Consulting | Enterprise Sales for Startups | $2M => $10M ARR

I believe that building a great company can be life-changing. 

I've seen it happen multiple times.  

I’m here to help founders bring their vision for their business to fruition. I know how much it takes to bring an idea into the world. You've already come this far, mostly through sheer force of will and the resources you had available. I can help you get to the next stage.  

I know that with the right things put in in place at the right time, you will be unstoppable.  

DM me if you want to talk about your business.

6 months in, your new sales hire hasn't closed a deal…

Here's what happened:

→ You posted a job for "experienced AE" (experienced in what?) 
→ Hired someone with who knows the industry 
→ Had them shadow 5 calls 
→ Said "start booking meetings" 
→ Bought whatever tools they wanted 
→ Waited for deals to close 

Each failed hire costs you $150K+ in salary and lost pipeline.

The problem isn't the person. It's expecting them to reverse-engineer a sales process that barely exists.

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

Follow for more on sales, leadership and scaling.

Monica Stewart

Getting B2B SaaS founders out of survival mode through scalable revenue | $1M - $10M ARR

LI DMs I will *not* be reading:


1. Hi Monica, thanks for connecting! I noticed you help X do Y. Quick question….

2. Hey Monica….(long question about my opinion on AI or some other thought leader-y but generic topic)

3. Hi Monica, we help X through (our product). Would you be open to a 30-minute call to explore further? 

4. Hi Samantha, I'm reaching out because I think our conversations could be mutually beneficial. Let me know if you're open to exploring some new ideas.

5. Hi Monica, love your post on protecting energy. I’ve helped scale SaaS apps like (random company 1) and (random company 2) from prototype to revenue-ready. Would be great to connect and share insights.

What do these all have in common? Nothing at all to do with me. 

It’s crazy because LinkedIn is *the easiest* place to say something relevant. 

I post daily.
I have a company page and website linked. 
You can see all my connections.
You can even see what I’m saying on other posts. 

I’m not asking you to try harder, I’m just asking you to try a liiiittle bit. 

Is that too much to ask? 

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

I’m going to hold your hand while I say this…


You have the same competitors as everyone else in your industry and they win 65-75% of the time. 

Your buyer isn't choosing between you and nothing.

They're choosing between: 
→ You 
→ Building it themselves
→ Hiring more people to do it 
→ Doing nothing and living with the problem

What you think: "We're the only solution like this" 

What buyers think: "Is this worth the time, money, and risk?"

Your real competition isn't other vendors.

It's inertia, budget, internal politics and the 47 other initiatives fighting for attention.

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

Two reasons you will find me up at 4AM:




1. I’m partying 

2. I’m on my way to Pavilion GTM 

Today it’s the second one.

DM me if you’re there!

No alternative text description for this image

There are 5 types of startup founders (all problematic):

1. The Expert

Pros: You come from the industry you built your product for.  You have deep industry expertise and built your business to solve problems you personally experienced. 

Cons: You hire “domain experts” thinking industry knowledge = sales success. When this fails, you go the opposite route and hire an equally unqualified “sales expert” (sales bro) who will also not be able to sell your product. 

2. The Conservative

Pros: You have impressive metrics (profitable, high close rates) but don't realize you’re playing it too safe. You focus on optimization before expansion. 

Cons: Prefer incremental improvements over bold moves. You probably underestimate your own value. 

3. The Founder Under Pressure

Pros: Ambitious AF. You want Cursor-level growth and you believe you can get it. You hold yourself and your team to high standards and are always looking for new and better ways of doing things. 

Cons: You also might be under pressure from investors with borderline unrealistic expectations. You're caught between needing rapid growth and the need to build systems that be sustainable. You’re quick to hire/quick to fire and end up wasting time and money on bets that ultimately don’t work out.

4. The “Revenue Solves All” Founder

Pros: Extremely sales and revenue focused. You are always on, always hustling and always closing. 

Cons: You’re working hard but maybe not smart. Your impressive pipeline is hiding churn issues, low conversion and inconsistent sales process. The more you ignore deeper issues, the more new leads you need to cover them up. Eventually this strategy breaks. 

5. The Single-Motion Founder

Pros: You’re fearless and go all in when something works. You’re great at finding the repeatable case study that will take you to $1-3M.  

Cons: You don’t know when to switch it up. Enterprise sales is just SMB sales to bigger companies, right? Partnerships - sure, how hard can it be? Your ability to FITFO starts to drag you down when you have to solve bigger problems, and more of them at once.

Which one sounds familiar to you? What did I miss? 

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

My first sales job was getting strangers to give me $1000 in 15 minutes. 



I did nonprofit fundraising. You know those people with clipboards trying to wave you down on the street? That was me.

Except I was going door-to-door in New York City. Inside apartment buildings. 

Buzzing random apartments hoping someone would let me in.

Most days looked like this: 6 hours of walking, 200 doors knocked, 150 no’s, 50 conversations, maybe 20 donations.

It was tough...but my team became the top earning office in the entire country.

Here's what we figured out:

When someone was willing to talk to us and cared about the cause, we didn't ask small.

Our training materials said to suggest $100 one-time donations or $15-20 monthly pledges.

I asked for $500-1000 upfront or $150-250/month.

And people said yes! 

Not everyone. But the ones that did made a HUGE difference.

I learned that when you find someone who is genuinely invested in the problem you solve, don't play small.

Asking for what’s actually needed makes it feel way better for the person to say yes.

Most reps undercharge because they're scared of hearing no.

I was getting 150 no's a day anyway, might as well go big on the yes.

What non-sales job taught you the most about selling?

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

ONE bad sales hire costs hundreds of thousands in comp and millions in lost revenue and pipeline. But we're still winging the interviews. 

"They seem like a hunter"
"He's a really nice guy, good culture fit"
"She doesn't have the experience but I could see her getting along with our clients"

......None of these are reasons to hire someone. 

What are? SO glad you asked! Jason Lalk and I talked about this a few weeks ago and you can listen to the whole thing now....check the comments. 

—————————
👋 Hi, I'm Monica Stewart. I help B2B SaaS founders grow revenue from $1-$10M ARR. 


If this is you, send me a DM

(2) Notifications | LinkedIn

li_at

JSESSIONID

Talks about #b2bsales, #feminism, #startups, #negotiation, and #enterprisesales

Dear people of LinkedIn/TikTok/Instagram,



It’s “lose”, not “loose”.

Pique = generate curiosity 
Peek = take a small look
Peak = the height of something 

(3 words, 3 different meanings)

There is no such thing as “ChatGBT”.


Sincerely,

An elder millennial word nerd

I’ve helped dozens of startups grow to $10M in revenue. There's on pattern they ALL have in common: 

Stage 1 ($1-3M): Perfect one thing

One ICP, one use case, one sales motion
Don't build enterprise features when you're selling to SMB
Don’t try to sell to SMB when you built for enterprise

Stage 2 ($3-5M): Scale what works

Hire more people to do the thing that's working
Add one new channel or segment (not three)
Build systems around what’s working

Stage 3 ($5-10M+): Add complexity

Verticalize, add product lines, expand geographically
Add specialization (SEs, different sales roles, etc.)

The mistake: Trying to do Stage 3 activities at Stage 1.

I see founders building enterprise sales teams when they haven't figured out how to convert the pipeline they have. 

Hiring VPs when they need individual contributors.

Trying to growth hack instead cultivating consistency. 

Everything feels hard when you're trying to solve tomorrow's problems with today's resources.

—————————
👋 Hi, I'm Monica Stewart. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

10 ways to f*ck up a pilot:
👇

1. No end date

2. Don’t talk about pricing beforehand

3. Kick it off w/ a 90 min group “training”

4. Always extend for as long as they need

5. Send emails asking if they’ve “had a chance to play around with it”

6. Don’t send any emails at all 

7. Wait until the end to find out how it went

8. Believe a pilot will give your champion the ammunition they need to talk to their boss

9. No defined goal (they’ll see the value for sure once they use the product)

10. Send 8 support videos and a 40 page deck after the kickoff

What did I miss?


—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

How I protect my energy as a solopreneur: 

- No notifications for anything ever 
- Being a Leo/Scorpio (generally unbothered)
- Blocking people fast
- Having a small weekly window for "coffee chats" 
- Learning to love boundaries
- Incense and candles in my office 
- Getting the nice coffee
- Prioritizing sleep 
- Hydrating
- Treating commitments to myself as seriously as those to others
- Filling my space with plants and flowers 
- Long walks to decompress 

What about you?

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

"We've exhausted our entire market. There's literally no one left to sell to."

This is what a founder told me (with complete conviction) at $3M ARR. 

They had a 15% close rate. $5k ACV. 200-day average time to close-lost a deal.

The problem wasn't their market. It was their belief system, which was seeping into every part of the way they sold. 

Their prospects saw them as a nice-to-have, and they had been struggling for long enough that they started believing it too.

We made two changes:

1. Ruthless deal qualification: 
50 days to win a deal, 200 days to lose one. The "lost" deals were never real deals, they were prospects the team refused to disqualify out of scarcity. 
We started saying no faster to focus energy on actual buyers.

2. Doubled the price: 
From $5K to $10K immediately. The low pricing screamed "we don't believe in our value" and attracted junior level prospects with no real authority. 
Higher prices forced us into conversations with people who could actually buy.

Six months later: 
=> ACV hit $15K. 
=> Close rates improved. 
=> Sales cycles shortened. 

We signed an $80K strategic deal (biggest to date) and had 6 more deals over $50k in pipeline.

There were plenty of qualified buyers in the market, but they weren't showing them the right signals.

What would happen if you doubled your prices tomorrow?

If they wanted to, they would, except…


=> They had 7 other meetings the day you did your demo
=> Your recap email was 5 paragraphs 
=> You’re making them have another 30 min meeting before you will give pricing 
=> You keep asking "when can we get this signed?" 
=> You haven’t talked about implementation at all 
=> You scheduled a "quick 15-minute call" that turned into an hour 
=> Your demo was the exact same generic tour you give everyone (after a 45 min discovery call)  
=> You send them case studies with no context 
=> You keep mentioning how "this deal needs to close by end of quarter"

What did I miss?

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

Walmart makes $680B a year but you still have to fight to get them to give you $100k. 

What enterprise buyers actually look at (but won’t tell you):

→ Can you win over internal builds and incumbent vendors who say they do the same thing?
→ Will you still exist in 3 years?
→ Can their team actually implement this?
→ What happens if you get acquired or shut down?


What's in your sales deck: 

→ Product differentiators 
→ Your roadmap 
→ Your founding story + investors 
→ Other big client logos you have


Large companies are slow to sign because of bureaucracy and slow to decide because the cost of being wrong is massive.

If you are not addressing all of this in your sales process you will leave millions on the table. 

—————————
👋 Hi, I'm Monica Stewart. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

LinkedIn

Sales Navigator

Highly unscientific ranking of milks (and what they mean about you):

Raw Milk: 0/10 
Tell me you’ve never seen a cow without telling me. Probably an RFK fan. 

Pistachio: 10/10
If you like this milk, you are 100% fancy AF and 100% my friend! 

Coconut: 9/10
The second choice behind pistachio. If you’re a coconut fan you definitely have good taste and a go-to espresso drink order. 

Soy: 6/10
This is the OG non dairy option but is very hit or miss these days. If you drink soy milk you probably started in the mid-2000s and just never switched. 

Almond: 3/10
Non dairy milk but let’s make it as environmentally unfriendly and weird tasting as possible. I’ve never met anyone who actually prefers almond. 

Cashew/Macadamia: 7/10
More points if it is made in-house. Probably does not taste as good as coconut or pistachio but a worthy option! If you like this milk, you definitely compost. 

2%: 1/10
Why, just why. Not good for you and doesn’t taste like anything. If you order 2% you probably describe yourself as a “political moderate” and may have voted Republican. 

Half and half: 4/10
Not preferred, but definitely the only acceptable choice if you’re at the bodega or diner and there are no non-dairy options. 
If half-and-half is your go-to you may have grown up on the East Coast and/or order your coffee “light and sweet”

Is this accurate? What did I miss?

We doubled close rate in 90 days - without adding new leads. 


Before: 

→ 30% of "opportunities" had no recent activity
→ Average discovery call talk time was over 60%
→ No agreement on what a qualified deal looked like
→ Reps chasing unqualified/unresponsive leads for months

After: 

→ 5-step discovery framework 
→ Deal scoring to align on what qualified is  
→ Switched to 45-minute “demoscovery” calls for smaller prospects
→ Closed/lost quickly - no points for stale pipeline

Tools used: The same ones they already had.

Result: Pipeline quality improved dramatically. Close rate went from 12% to 31%.

The fundamentals are the cheat code you’ve been looking for.

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

THE BETRAYAL


- Every new AI tool that I have to pay $140/year for
- Broken espresso machine 
- “Sorry, we didn’t have a chance to look at the notes you sent before this meeting”
- Viral LI posts about pancakes 
- Airport security workers at 6am who act like you’ve never seen a TSA line 
- Disappointing breakfast sandwiches 
- My new plant that hates every corner of my apartment 
- When you think it’s going to rain and then it doesn’t 
- Winter in NYC
- Uncooked egg whites 
- Microsoft Teams 
- SharePoint 
- Google Meet 
- No guestlist (?!?!)
- Boomers 
- Air fryers 
- The $200k SDR
- Ranking Cuomo
- When your headphones die
- Chicken nuggets

Are you with me?

How many plants is too many plants?



I cannot stop buying them, and unfortunately I have no intentions of trying to stop either.

(I have 31 plus these two new cuties).

Totally reasonable, right?

I've flown out of all 3 NYC airports in the last 30 days. Here is the ranking no one asked for:


JFK

You’re going to love or hate JFK depending on what terminal you go to and when you fly. 

Early morning flight from Terminal 4, 5 or 8? You’re good.  Evening flight during any holiday and you will be hating your life. Bonus points for Terminal 4 (Amex and Chase lounges right next to each other so you can go wherever is least crowded). Minus points for making you take a SHUTTLE to a special lot to call an Uber. 

Best places to eat outside lounges: Piquillo and Deep Blue Sushi in Terminal 5, Vino Kitchen and Flatiron Coffee in Terminal 4. 

If you have a long layover or enjoy hanging out at the airport, check out the vintage TWA Hotel also! 

LGA 

LaGuardia used to be Penn Station but with less of a vibe, but it got a massive upgrade in the last few years and is now totally not embarrassing. Plus a car here from downtown Manhattan is about half the cost of going to JFK. 

Security lines are usually very short and they now have a Centurion Lounge! LGA is my top choice in almost any situation. 

Best places to eat outside the lounge: Orpheus + Apollo, Bar Veloce, Beecher’s (iykyk), Talde

EWR

Just….no. Newark is THE WORST. It takes forever to get to. You can either take an Uber for $100 or take 2 trains and a BUS. 

The baggage handlers are apparently all training for some kind of sport using our luggage, because I have had 3 suitcases damaged here. There is no Centurion or Chase lounge. 

They are chronically understaffed and it’s so bad that your airline will text you to warn you if you are flying out of there.

Best places to eat outside the (limited) lounges: Nothing. Just go to Shake Shack I guess?

What do you guys think - accurate?

I used to think successful founders knew some secret I didn't. Like there is some sort of ancient tribal knowledge that makes VC give you money. 

Then I started working with 50+ SaaS teams and realized the truth:
The successful ones weren't smarter. They just said "no" to more things.

The struggling founder:
=> Building enterprise and SMB features simultaneously
=> Hiring sales AND marketing at the same time
=> Chasing 5 different customer segments

The successful founder:
=> Picks one customer type and dominates it
=> Hires one function, gets it working, then adds the next
=> Says "not yet" to unaligned opportunities

The difference isn't intelligence or resources.

It's the discipline to focus on one thing long enough to make it work.

Most startups don't fail because they picked the wrong strategy.

They fail because they never executed any strategy completely.

—————————
👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. 

If this is you, send me a DM

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