OpenEd.co

( )pening the world of education for every learner. OpenEd is the home of the OpenEd Daily, the OpenEd Podcast, and our programs serve 12,000+ students with our open education model aimed at transforming millions of lives across the United States. We help families and schools help their students reach new heights with their individualized needs.

Partner & Chief Operating Officer

Liberty Ventures

Investor, Limited Partner & Advisor

Reveal

Reveal and Crossbeam merged June 24, 2024 in the biggest news in partner tech history!

Chief Partner & Ecosystem Officer (merged with Crossbeam)

nearbound.com

Formally PartnerHacker (acquired by Reveal, 2023), Nearbound.com is the media company covering the news, stories, tactics and experiences of the Nearbound Era. 

Nearbound makes the world go ‘round.

Co-Founder & CEO (acquired by Reveal)

Nearbound Podcast

The number 1 podcast in the Nearbound Era - The Nearbound Podcast

Producer & Co-Host

Cloud Software Association

Member, Board of Directors

Pillar

Member Of The Board Of Advisors

University of South Florida Muma College of Business

Member of The Board of Advisors, Guest Lecturer

Curu

Drift

A LinkedIn Top 50 Startup for 4 years in a row, Drift is one of the fastest growing B2B SaaS companies, ever. 

As Drift's first ecosystem executive, I was responsible for creating and scaling the Drift Ecosystem through global channel, strategic alliances, technology partnerships, and integration of Drift's GTM engine. Built Drift/Adobe Alliance from zero to Adobe Partner of The Year. 

Creator of the Conversational Marketing Blueprint - the underlying methodology used to certify thousands of marketers on Conversational Marketing.

Creator of Conversational ABM - launched at Adobe Summit during the Keynote to an audience of 19,000+ people as the only non-Adobe company present on the main stage.

Founded Drift's Tampa Bay office, our fastest growing regional location. Sourced and hired recruiting leadership, customer support leadership, and sales development leadership that now supports over 50 employees and growing rapidly in the region.

Sr. Director, Global Partnerships (acquired by Vista Equity Partners)

Passion is the primary ingredient to my being. About me 👇

I forge movements behind undeniable shifts in the world.

I remodel companies from participants to change agents. 

I build teams who's careers are transformed by the audacity of an unshakable vision & intense pace.

Back-to-back unicorns (PandaDoc, Drift). Board experiences in capacity as an executive, founder, small investor, and advisor (and plenty of lessons from my failed startups too, of course). 

Co-Founder of PartnerHacker (acq 2023), Co-Founder of Nearbound.com, Chief Ecosystem Officer at Reveal, and currently leading the nearbound industry in the best ecosystem in B2B - the partnerships ecosystem.

Always willing to help those who ask. I've taken hundreds of calls with first time entrepreneurs, revenue leaders, and partnership professionals. Help first, good follows. 

Play long term games with long term people 🤝

Jared Fuller

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

Making enterprise revenue predictable for B2B SaaS founders. 

If next year’s revenue, your next hire, or your next 20 customers feel like a gamble, you’re not alone. 
Most founders don’t see the real cause... inconsistency across sales, hiring, and leadership.

I help you implement repeatable enterprise sales systems that remove that guesswork. 

Book a 30‑min strategy session at the link below. We’ll diagnose the single biggest inconsistency costing you predictability. (Shortened sales cycles by 50% for a recent client.)

Monica Stewart

I lost a $227K deal because I made the CTO look stupid 😬


8 months working on this deal. Perfect use case. Everyone loved us.

Then I pulled up my slides showing how much time they were wasting with their current process.

Turns out the CTO had personally championed their current system two years earlier. Like, sold it to the board and managed the implementation.

And I (some random salesperson) just made this whole presentation explaining why it was inefficient.

The deal died two weeks later.

"Budget priorities shifted".

What I learned:

People don't want to be told they made a bad decision (especially not by someone who has never had their job). 

They want to be shown how to make a good one going forward.

"You built something great for where you were. Now you're ready for what's next."

Evolution, not replacement.

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

Making enterprise revenue predictable for B2B SaaS founders | $1M - $10M

Sometimes you meet people who make everything around them better, just by existing. 


Leslie Venetz is one of those people.

Leslie is an expander. She is the biggest champion of her friends, the most generous anti-gatekeeper, and relentless supporter of women. 

Leslie is the kind of person who knows a million cool people and is always conspiring behind the scenes to get them to be friends with each other and she is ALWAYS RIGHT (Anne Pao Laura Erdem ⚡Shannon Plumb⚡ Alice Heiman Chris Tubis). 

Watching Leslie write Profit Generating Pipeline over the last year and launch it into the world has been SO INSPIRING and it was sooo much fun to celebrate it with her last week 🖤 

Congratulations leslie and thank you Meg for introducing us. 

No better feeling than seeing your friends winning.

Ok let me get this straight...


Everyone should use AI.
But not to write LinkedIn posts.

BUT you should be writing about AI because it’s the future.
If you use AI for writing you’re lazy. 

But if you don’t use it for everything else you’re living in 2015. 

Cool cool cool. 

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

When I was a kid I didn’t know anyone who had a corporate job. 


I’m the only person in my family to graduate college. 

I wasn’t even planning to go. I only applied as a way to get out of the city I grew up in. 

If you would have told 15 year old me that I’d end up building a business helping startup founders sell to the biggest companies in the world, I literally would not have known what you were talking about (and probably gone right back to listening to Wu Tang Clan). 

I went to Brooklyn College because I wanted to be in NYC (despite having only been there once for 5 days). 

I studied International Relations and worked my way through school. 

I got a job selling hedge fund conferences after graduating because it paid the same as all the other jobs BUT had commission. I made $36k my first year. Got a crash course in selling to people WAY above my pay grade from Jared Rose 

Switched to financial services for a 40% pay bump, realized I made a terrible mistake after a year. 

Went to work at an art tech startup and started freelancing for conference companies on the side. 

Got my first SaaS sales role and made $150k my first year. I stayed 5 years and learned everything I could about sales, logistics, supply chain, economics and how enterprises really work. Got to test so many things with Erika Borden and build a great team with Peter Swartz and Keith Soura 

Moved into leadership and ran teams at 2 more startups. Got to work with amazing people like Kristen Habacht Alexa Battista and Hamid Palo

Realized my destiny was not working for other people and went into consulting, still ended up working for someone else to build an agency. So many lessons learned about consulting and scaling with Matt Lopez Franklin Williams Jake Dunlap 

Took a 2-year sabbatical to travel the world, organize raves and DJ. 

Finally went all in on myself. I made more in my first year than I ever did working for someone else. Learned a ton (and still am) about brand, social, business models and sales from Ken Yarmosh Reshia Lea Colin Stewart-Perreault 🧙 Leslie Venetz Meghann Misiak 🔮 Scott Sambucci

Along the way, became obsessed with building a great business and helping founders do the same. 

15-year old me would be PYSCHED if she knew all this was possible. The only reason I got here was the people who helped me along the way. 

Who's helped you get where you are today? 

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

If you're a Series A-ish startup with enterprise customers, you have two paths.


You cannot do both at the same time.

Most founders try anyway. And it kills their momentum.

Your first enterprise deals are almost ALWAYS proofs of concept. 

You're not capturing full value in year one because: 
→ Your team does not have the patience for a 7-figure sales cycle 
→ Your customer isn’t fully committed yet, they want to see what it's like to work with you first

So you have to choose a path. 

Path 1: Stack logos at lower ACVs 

→ Close lots of enterprise customers at <$50K/year 
→ Prove you can win deals consistently 
→ Build a diversified customer base 
→ Go back later for expansion

Path 2: Go big with anchor accounts 

→ Close a handful of customers at mid-6 or 7 figure contracts
→ Prove you can build very deep enterprise relationships 
→ Get real partnerships 
→ Extract maximum value upfront

“But Monica we want to run both plays and see what works better.”

…..no. 

These require completely different team structures, sales motions, founder involvement, GTM investments. 

Your company will look entirely different depending on which you choose.

If you choose Path 1, you might wait too long to expand and end up leaving a lot of money on the table. 

If you choose Path 2, you might become a consulting firm building custom features for 3 big customers instead of a scalable product.

TL’DR: Pick ONE. Get really good at it.

Then tackle the other.

Which path are you on?

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

No alternative text description for this image

VPs of Sales who won’t answer cold calls even though THEIR OWN TEAM MAKES COLD CALLS...


Beyond rude, right? 

Except I teach all my teams to leverage social selling…and I also don't reply to 95% of LI DMs from sellers… bc they are hot garbage and not at all relevant to me. 

I even sent a sassy email reply to someone recently because they cold emailed me 3 days in a ROW about something I didn't want, and it was annoying. 

Am I the problem? Maybe. 

But there is also an element of this conversation that feels like “wHY arE WoMEN on DatInG AppS BUT wOnT TalK To a RaNDom Guy At A BaR??”

No one owes you their time, even if you're broadly on the same team because you're both in sales. 

Sales leaders, don't be jerks, but also sellers, would YOU respond to you?

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders


Follow for more.

Sales Navigator

li_at

JSESSIONID

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

"Anyone had luck getting out of a contract with (sales tool we all know)? We're 1 year into a 3 year contract and no one on my team cares about it."


😬😬😬

Saw this from a CRO in a private Slack yesterday.

This is why your onboarding experience matters so much.

It sounds boring. It's not boring. It's the hidden thing causing you to leak revenue.

Most teams close a 3-year deal, celebrate the win, and hand it off to CS. Do a “training” for the users. Maybe QBRs. 

And 12 months later, the customer is looking for the exit because no one on their team knows why they should use the product.

How to make sure this doesn’t happen to you: 

1. Schedule the kickoff when you sign the contract
Don't send an email intro from sales to CS and hope CS schedules it.
Get it on the calendar immediately.

2. Give CS everything they need from the sales process
What does the customer actually want to accomplish? What's the most important thing for them to do first? What are the risks on this account?
Should go without saying. But most teams aren't doing this.

3. Onboarding is NOT a product walkthrough
It's not training on features.
It's showing them how to do the thing they bought the product for.
So know what they bought it for. And show them how to do that thing.

Bonus - make it interactive! 

Structure onboarding as a multi-part workshop.
Roll out components in phases so by week 3-5, they've created something tangible they can show to the person who signed the contract.
Give them a win in the first month.

4. Create superusers 
Now they have basic knowledge, where do you go from here? 
Send advanced usage tips, mini videos, new product release messaging customized for them (not the mass email you sent), social content, tips from other users. Doing this even once every 1-2 months makes a huge difference. 

5. Make QBRs internal show and tell 
Usage stats are cool. 
Making your users look amazing by showcasing their work is even better. 

What did I miss?

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

"My sales team isn't hitting goals but I'm not 100% sure why"


I know why. And it's probably not your team.

Here's what I see over and over:
Founders blame their reps when close rates are 12% and outbound response is 1%.

But when I ask "Has anyone ever been successful with this process?" the answer is no.

Your team isn't the problem if:
→ No one has ever hit quota using your system 
→ Your close rate on "qualified" opportunities is under 20% 
→ Your outbound gets 1% response rates 
→ Your reps don’t know what they are supposed to do on any given day

You don't have underperformers, you have a broken system (or none).

If you've cycled through 3+ reps in the same role and they all "underperformed," they were not the problem.


👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

I switched to flying business or first class ONLY a year ago (as a solopreneur). It's not even that expensive...and here's what happened:


1. I made friends on the plane! 
Met someone on the way to SF going to the same conference as me and shared a ride, found a wine + writing buddy on the way to Mexico City 

2. I started going to the airport early
I had lounge access w/Amex before but would usually arrive just on time to board. Having more lounge options + actually looking forward to being on the plane motivated me to get there earlier. Way more relaxing and productive 

3. I actually got work done 

Me on every flight: I’m going to get so much done! 
Me as soon as I try to open my laptop on a tiny angled tray: F*ck this I’m going to sleep

Having extra space and no one’s elbow in your lap makes it soooo much easier to focus. 

4. I feel more confident 
Running your own business is hard work, and I work really hard. Giving myself a nice experience when I travel is such a nice little treat and reminds me that I’m actually doing pretty well. 

BONUS: It’s not even that expensive. Here’s how I pay for it: 
- Points stacking (all dining/grocery expenses go on Chase card for 3x points, everything else on Amex)

- Search by point value, not price. I go to PointsYeah first to see which flights have good points deals, then book that flight directly with the airline. 

- If there aren’t good points deals, I pay for the basic fare through the credit card portal then upgrade with points. 

- Points bonus cards! I’ve gotten 200k points this year by opening 2 new cards. Spend the minimum and pay them off immediately. 

- Pay attention to airline upgrade offers. This summer I paid $500 for United Flagship First from NYC-Rome by upgrading a flight I got with points. 

What’s your take - biz class worth it? Do you use points?

👋 Hi, I'm Monica Stewart. I help B2B SaaS founders grow revenue from $1-$10M ARR. 
If you’re on this journey, send me a DM!

You might lose enterprise deals because you're too small, but you will definitely lose them because you're too risky.

And you keep making it worse...

- Talking about how fast your team moves and releases new products
- Explaining in great detail your cutting-edge technology that no one else has or really understands
- Emphasizing how different you are from incumbents 
- Offering "flexible pricing models" (aka we haven't figured this out yet) 
- Putting your founder on every demo 

Yes, enterprise buyers are attracted to you because you’re exciting. But they sign with you because you’re dependable. 

The legacy players aren’t winning because they're better.

They're winning because buying them makes no one look bad. 

Build trust first. 

What do you think? 

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders


Follow for more.

8 startup lies: 


“We just need to scale the team”
=> The last 3 people we hired didn’t work out, but we’re betting that the next 3 definitely will

“Enterprise customers love us”
=> We’ve got 12 enterprise logos that are all underpaying, and haven’t spoken with us in 5 months 

“We have strong pipeline growth”
=> Several intro meetings with innovation teams who said they’d circulate internally and get back to us

“Our product sells itself”
=> We run 80-minute demos and talk 80% of the time and then get ghosted. Everyone knows what our product does and no one knows how it would help them

“We have a great sales leader with experience and a rolodex”
=> We are wildly overpaying someone to have introductory meetings that go nowhere. They haven’t closed anything in 8 months. 

“Our product is easy to use”
=> Founder is still answering support tickets because we can’t train anyone else to do it

“We have great investors”
=> At the last board meeting our investors told us to switch to PLG, now they want us to hire 8 more salespeople by Q1 

“We’re on track to triple revenue again this year”
=> We haven’t made an actual forecast yet and have no idea what our number is, let alone how we’re going to hit it

What am I missing?

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders


Follow for more.

The best salespeople talk about risks more than benefits…but not in the way you think.


✖️ "If you don't implement our data tool, your sales team will spend hours on manual work instead of closing deals."
✔️"Your incomplete CRM data means your marketing team is guessing at messaging. That's why your ads aren't converting. This will be a blocker to your growth if you don’t improve your data"

✖️"You're overspending on recruiters without our solution."
✔️ "You don't have a company LinkedIn strategy. That's why you can't fill senior roles and keep losing candidates to competitors."

What great salespeople understand...cost of inaction isn't what they are missing out on. 

It's about connecting your solution to an EXISTING problem that already has its own velocity.

What do you think?

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

You’ll never see me talk about this on LinkedIn….


- Sports 
- My kids 
- What my kids playing sports taught me about B2B sales
- What sales bros you should follow 
- Sales lessons from $2B orgs 
- Biohacking
- Taylor Swift
- Sales tips from the 90’s
- XYZ thing that is dead 
- AI hype 
- Fear-based sales strategies 
- A conversation I had with a fake CRO of a fake $500M org

What I will never stop talking about:

- Brilliant women 
- Burning Man
- Women you should follow
- Pushing yourself to grow 
- Raves 
- Real life sales lessons from <$10M orgs 
- Empathy 
- Coffee in tiny cups 
- AI in the real world 
- How much Zig Ziglar still slaps
- The power of focus 
- Plants 
- The fact the no one is free until everyone is free 
- A conversation I had with a real founder of a real $6M org 

What’s something you won’t stop talking about?

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders


Follow for more.

How I know your sales team is about to crash out
Whether you want to admit it or not….


=> Your pipeline is 60% deals with no activity in 1 month or more
=> Reps spend more time on internal calls than customer calls
=> Your close rate is under 20% but you keep hiring more AEs
=> Holding on to every deal “just in case” 
=> “Sure, we can set you up with a trial”
=> No qualification framework, just vibes 
=> “No time to prospect”
=> Your sales manager is either on no calls or every call
=> The weekly sales meeting is always different 
=> You’re not connected with all your customers + prospects on LinkedIn

What did I miss?

👋 Hi, I'm Monica Stewart. I help B2B SaaS founders grow revenue from $1-$10M ARR. 
If you’re on this journey, send me a DM!

10 things buying software taught me about sales:


1. No one actually has internal meetings about a demo they saw 

2. Every decision involves 2-3 people (even in small companies)

3. People’s vision of who they want to be is just as important as what they actually need 

4. Do not underestimate the power of making it easy to say yes. The number of decisions people have to make in a day is insane. 

5. Arm your champion with a one-sentence answer to the question “what is this thing again?” 

6. The 12 page slide deck you sent most likely will not be read

7. People on the same team can have wildly different priorities 

8. Dark social is real. 90% of information comes from referrals, communities, DMs and texts. 

9. If they don’t think they need it at full price a discount makes no difference 

10. The trial access you gave will be used for 30 minutes, max

This is as a VP of Sales in 15-20 person orgs but I feel like applies most places. 

What did I miss?

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders
Follow for more.

The most cringe thing about me?


I am CHALANT AF.

I care a lot.

I’m not here for “passive income”

I’m not here to build a business I don’t have to work on. 

I’m trying. Like, really hard.

There are a lot of people on LinkedIn who talk about how to make money without trying. 

Grow revenue without talking to customers. 

Build a course instead of working with clients 1:1. 

Use AI agents + AI SDRs + vibe coding to build a SaaS business that runs itself. 

Work 4 hours a day and go meditate. 

I believe that the real flex is building your life around something that you love and care about so deeply that you want to lean all the way in and challenge yourself to commit to it even more. 

The real flex is making a life you don’t want to be detached from.

What do you think? 

👋 Hi, I'm Monica Stewart. I make enterprise revenue predictable for B2B SaaS founders

Follow for more.

Stoppp itttt. 


You're killing your enterprise deals by (accidentally) making buyers look stupid.

What you're doing: 

→ Showing slides about "common pain points" that describe their exact setup 

→ Asking "what are your challenges?" 

→ Pointing out how much better your solution is 

→ Highlighting what they're missing by not using you

All they hear is "You made a bad decision two years ago and you've been losing ever since."

You’re totally missing the fact that at least 3 people in that meeting either: 
→ Approved the current vendor 
→ Implemented the current system 
→ Trained everyone on the current process 
→ Built the workaround hack everyone uses

You just called their last two years of work a mistake! And you wonder why they ghost you after the demo.

Your first competition is the buying committee's ego.

Give them a way to look smart choosing you, not wrong for not choosing you sooner.

👋 Hi, I'm Monica Stewart. I help B2B SaaS founders grow revenue from $1-$10M ARR. 
If you’re on this journey, send me a DM!

linkedin.com

Daniel Garcia

If you spend more time talking about what you hate than what you love 



We probably won’t get along.

I don't spend money on retail.

 
Why? 

1. We already have too much stuff

Humans have already made enough clothes for the next 6-7 generations. There are literal mountains of clothes sitting in landfills around the world.
I don't need to add to that. 

2. I like nice things 

You can spend $100 on a new dress from Zara that is made from synthetic fabric, isn’t designed well and will last <2 years. 

Or you can spend $100 on a secondhand dress from a designer you love that cost $500 new, is made from real silk, fits amazing and will last 10 years.
Seems like an easy choice to me. 

3. Community over corporations

My desk is from IKEA but I bought it used on Craigslist. 

Once I factor in the time it takes to pick it up and an UberXL to bring it home, I could have bought it new. 

But, I’d rather give that money to a person in my city than to IKEA. 

4. I’d rather spend the money on other things

I do buy some things new (shoes, work bags, things I can’t live without). 

But I'd rather prioritize buying more BTC and spending on travel. 

Not brand new stuff I'll probably replace in two years anyway.

It's about being intentional with my money. 

What do you think?

P.S. My faves are The RealReal and Poshmark for clothes/bags, Craigslist for furniture and Whatsapp groups (huge in Mexico) for almost everything.

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Jared Fuller

Monica Stewart

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The Battle

Jared Fuller

Monica Stewart

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Monica Stewart's LinkedIn Performance

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