Co-Founder & Chief Revenue Officer at Sales Assembly | Developing the GTM Teams of B2B Tech Companies | Investor | Sales Mentor | Decent Husband, Better Father

I’ve spent my career trying to solve one puzzle: how do you scale sales teams without losing what makes them great?

Before Sales Assembly, I lived the highs and lows of hyper-growth - leading revenue teams, juggling targets, and realizing that growth without structure eventually collapses under its own weight. The lesson stuck: great teams don’t just grow fast, they grow well.

That’s the idea behind Sales Assembly. We built the preeminent skill development platform for B2B tech companies: part training, part community, part therapy for GTM leaders trying to do more with less. We help teams move faster, stay aligned, and actually enjoy the process of getting better.

Somewhere along the way, I also became a General Partner at VentureOn Partners, Chapter Head at Pavilion, and mentor with Techstars. I’ve spent a lot of time with founders and operators who are chasing the same thing: building something that lasts without taking themselves too seriously.

A client and friend once described me as someone who “builds community through authenticity,” which I’ll take as the polite version of “tells it like it is.” That’s probably fair.

Outside of all that, I’m a decent husband, a better dad, and a walking Simpsons encyclopedia (seasons 1–11 only, of course). I travel when I can, laugh often, and still believe a good team - and a good joke - can get you through just about anything.

Matt Green

Your champion just rewrote your proposal in language her CFO would approve. She texted you on Saturday with intel from a leadership meeting you weren't in. Know what that looks like? 

Someone whose bonus depends on your deal closing.


Here's how one AE in the Sales Assembly ecosystem figured this out: 

She was working a MM deal that felt solid but wasn't moving. Champion was responsive, took every call, forwarded emails to the right people. Standard stuff. 

Then during a casual convo, she asked something she almost didn't: "You seem really motivated on this. What's going on?"

Turns out the champion's quarterly bonus was tied to getting this exact type of solution implemented before end of quarter. Her leadership had made it a goal. She needed this deal to close as badly as the AE did!


Believe it or not, everything changed after that. The champion started coaching the AE on exact language to use with her CEO. Shared what the CEO had said in a recent leadership meeting and suggested weaving it into the talk track. 

She'd gone from supporting the deal to co-building the pitch.


That deal closed. They still text each other to this day.


Now think about what DIDN'T happen. The AE didn't uncover this through a formal discovery framework. Instead, she asked one human question in a moment where she was paying attention.

And that's the thing very few folks teach in champion development. You can MEDDIC until you're blue in the face, but the single highest signal indicator of whether someone will actually fight for your deal is whether their compensation, promotion, or reputation depends on the outcome.


When someone's bonus is on the line: 

- They don't wait for you to ask for introductions. 
- They set up meetings before you request them. 
- They don't pass your proposal to procurement. They rewrite it. 
- They don't go quiet between calls. They reach out with intel you didn't know existed.

A friendly contact responds when you reach out. A real champion reaches out when you haven't. 


Do this exercise this week: On your three biggest open deals, can you answer these about your primary contact: 

1. What happens to their compensation or visibility if this project succeeds? 
2. What happens to them personally if it stalls? 
3. How are they measured on the initiative your solution supports?


If you can't answer those, really think hard about whether you actually have someone who will fight for your budget line in a room you're not in.

Sales Assembly facilitator Jon Rydberg nailed it: if there's no clear winner or loser when a deal dies, the deal is going to die. 

You can set your watch to it.

Co-Founder & Chief Revenue Officer at Sales Assembly | Helping B2B tech companies improve sales and post-sales performance | Decent Husband, Better Father

A CS leader in one of our peer groups tracks everything. NPS, CSAT, adoption, etc. Still got blindsided by three ENT churns last quarter. Combined $840K ARR = gone.

They had oodles of data at their fingertips, but they were measuring the wrong kind.

NPS tells you how customers felt last quarter.

Support tickets tell you what broke last week. 

Product adoption tells you what they did last month. 

All LAGGING indicators. By the time any of those metrics move, the decision to break up with you has already been made.


Leading indicators tell you what's GOING to happen. And there's real research backing up what stuff actually predicts churn before it shows up in a dashboard somewhere.

Login frequency is the most obvious one and the most ignored. HubSpot found that targeting users who dropped below one login per week cut churn by 15%. 

If someone stops showing up, the clock is ticking.


But logins alone miss the picture. Feature breadth matters more than raw engagement. 

Customers using 5+ core features churn at almost 1/3 the rate of single-feature users. The depth of adoption creates pain in the ass switching costs that no competitor can easily overcome. 

If your CSMs aren't tracking which features each account actually uses, they're flying blind on stickiness. And that's a shitty place to be when renewal season hits.


Another big one: WHO is logging in, not just how often. 

When admin and decision-maker engagement drops but regular users keep humming along, that's often the clearest signal your customer is shopping around. 

The people with budget authority are quietly shopping while their team keeps using your product out of habit. By the time the regular users notice, procurement already has three proposals on their desk.


The move here is to build a lightweight early warning system around 3 things. 

1. Login frequency trends by week, not month. 
2. Feature adoption breadth per account, tracked against your core value workflows. 
3. Stakeholder engagement patterns, specifically whether the economic buyer and admin users are still active or going dark.

None of this requires a new $100k CS platform. Pull login data from your product analytics. Cross-reference feature usage against your top five value-driving workflows. Flag any account where decision-maker activity dropped in the last 14 days. 

One Salesforce formula field or a simple dashboard in Gainsight or ChurnZero can automate most of it.

Lagging indicators tell you what's broken. Leading indicators tell you what's breaking.

While you can still fix it.

Leslie Greenwood

Chief Evangelist, Community Strategist, Co-Founder of Wednesday Women, Startup Advisor, Ex-Stay-At-Home Mom

I'm the Co-Founder of Wednesday Women and the Founder of Chief Evangelist Consulting: two ventures grounded in a core belief: community isn’t a tactic, it’s a force.

Wednesday Women began as a ripple in 2023 as a small, intentional effort to elevate executive women. We amplify women’s voices on LinkedIn, on stages, on podcasts, not as polished personas, but as their real, remarkable selves (the woman behind the title). Our public platform is for everyone, and we’ve built a private membership for executive women who want to go deeper with that mission and create connections both help unlock challenges but also are their biggest cheerleaders. 

Through Chief Evangelist Consulting, I help companies design community strategies that create lasting engagement. With 20+ years in customer-facing leadership roles, I approach community as a strategic lever, rooted in trust, value, and connection.

At the heart of everything I do is a belief in the power of evangelism, authenticity, and shared momentum.

And yes — I run on coffee, dark chocolate, trying (and failing) to keep me very vocal dog in check and talking loudly about diversity in tech.

Ambassador

Advocating for Pavilion’s mission of helping every leader and their team achieve their professional potential through community-powered learning. I will be supporting key initiatives, developing and teaching curriculum for Pavilion University and providing over 10,000 members with leadership advice. Join us at joinpavilion.com.

I couldn’t find any women experts. 
I don’t know any women speakers. 
I didn’t realize I built an entire exceptionally homogeneous event. 🤯

Seems to be a good day to remind everyone that if you’re looking for expert speakers for your event, I have an easy resource. 

Go to a certain website that might be where I work.  

Hit “Get Involved”

Hit “Find Speakers” 

Search a list of over 300 executive women. Ungated, free, keyword searchable.  

Reach out to them and say you found them thru Wednesday Women.  

Kinda easy actually. 


#noexcuses #nomoremanels #executivewomen #keynotespeakers

Leslie Greenwood 

💜 Bringing public awareness and private support to executive women, Co-Founder of Wednesday Women, Community Strategist, Chief Evangelist, Startup Advisor, Ex-Stay-At-Home Mom

🗓️I’m posting this on March 1 on purpose.

Because honoring Black women should never be confined to the shortest month of the year.

And as the mother of two amazingBlack women, this is personal for me.

Black History Month may end on the calendar, but the brilliance, leadership, influence, and impact of Black women do not.

So rather than letting the moment pass with February, I want to carry it forward.

I’m grateful for the Black women whose voices shape conversations, challenge assumptions, build companies, lead teams, create culture, and move all of us forward.

Not just in history.

The work is to keep noticing, keep crediting, keep amplifying, and keep showing up long after February ends.

March 1 felt like the right day to say that out loud. 💜

#BlackHistoryMonth #BlackWomenInLeadership #WednesdayWomen

29 new friends 
15 Wednesday Women members 
2 board members 
4 states 
A flight delayed until 4am 
Tears and cheers for a long awaited job offer. 
A gator 
Service beyond expectation 
Not only beautiful wines but the science and history behind them 
Local women artisan vendors - the honey chocolate 🤯
A celebrity chef - yes I got a selfie!! 
Gifts galore 

The biggest gift? 🎁 

Seeing these women take time away from demanding jobs, new babies, intense job searches and their families just for themselves.  

A little restoration, weaving the spider webs of connection, and possibly that well needed nap on the way back to the city.  

As one member said more than once, “I’m proud I’m putting myself first.”  I couldn’t have said it better myself.

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Breaking all the LinkedIn rules tonight!  

You know why? 

Too many exciting Wednesday Women events.  

2/20 - Denver Coffee - https://lnkd.in/g9mxhUqG

3/11 - Come spend the day in Napa with us - https://lnkd.in/gnDxz773

3/12 - SF Coffee - https://lnkd.in/gk2v94aH

3/26 - Anchorage Coffee - yes I’ll be in ALASKA and no I’m still not buying a coat -  
https://lnkd.in/gxMXKSeq

4/1 - Dinner in Seattle  - Regustration up by tomorrow here - https://lnkd.in/gg68APf2

4/15 - Dinner in Austin - https://lnkd.in/giWj4BPa

4/15 - 4/16 - Join us at SaaStock in Austin 

4/20 - Dinner in Dallas - https://lnkd.in/gXxx9XYW

5/8 - Dinner in SF - Details coming soon. 

5/13 - Dinner in San Mateo - Details coming soon.  

Middle of September - Dinner in Chicago - Details coming soon. 

Middle of September - Boston for Inbound 👀ing for a partner for an executive dinner! 

November Conference activation at ZERO-IN

Thinking about how intimate, curated events drive meaningful results? We have a point of view.  Our partners might agree 😉.  Happy to chat! 

If you’re an executive woman looking for meaningful connections, look no further.  💜

So you show up at the coffee shop you made a reservation for your event 15 minutes early as requested and no one is there. 

🚫 It’s closed. 
Lights are off. 
20 women are mingling outside.
Probably an event planner’s nightmare.

But they don’t have “Super Sam”! Samantha Archuleta found us an alternative location within five minutes that would be setting up our table on our walk over. Amazing! 

Sometimes things are just meant to happen. Our coffee was delicious, we got in a few hundred extra steps, we still had an amazing time learning about each other and finding ways we could support one another. 

And the extra bonus? Avotoasty is a woman owned business. Thank you to Sofia Guglani and your amazing team for working on the fly and helping us have an amazing event. We will absolutely be back. 

Robyn, Gwyneth Borden, Michelle Ji-Yeun Kim, Annette Sung, Holly Hon, Paula Mantle, Christina Mitine, Christina Singh, Aimie Vargas. Barbara Leavitt, Frankie, Michelle King, Gurlene Kaur, Arvita Tripati, MBA, Nellie Wartoft, Jieun Lee, ⚡️ Lori Dunn , Heidi Dickert, Mabel Liang

❓Who are the women in enablement I should know?

I’m looking for women who deserve more spotlight for the work they’re doing to help teams perform, influence strategy, and drive real revenue impact.

In my opinion, a lot of women in enablement are doing work that goes far beyond what the title suggests. They’re building the systems and momentum behind high-performing revenue teams. 

Honestly, many of them look a whole lot more like “revenue activators” than the traditional label gives them credit for.

And yet, some of the most strategic people driving revenue are still not getting enough visibility. 🤨

Let’s change that. 💜

Tag them in the comments or send in a nomination.

#womeninenablement #wednesdaywomen #revenueactivators

Now, how did Starbucks know that I was going on a work trip this week? #ubecoldfoam for the win.  

Wednesday Women nails representing.  

Bye Dallas, hello San Francisco and Napa! 💜

Let the travel hacks commence.  

1) Buy Wednesday Women purple suitcase because you saw it in the Morning Brew newsletter (brand partnership? 🤙😁💜).

2) Order your coffee as you’re driving into the airport or as you’re deplaning.  No long  line to then wait forever for your coffee.  Girls gotta have caffeine first thing.  

3) At least in Dallas, you no longer have to go to the airport to get TSAPreCheck. I got mine at Staples. #gamechanger 

4) When you’re traveling, do “community “everywhere”. Meaning reach out to your community and set up coffee dates.  I’m in SF and have coffee and dinner already planned for tonight.  Also 2 coffees and drinks set up in Seattle at the end of the month.  These are outside of our official events.  

5) Bring a good book. I’m always thinking about the experience and psychology of our events and reading Unreasonable Hospitality is taking this to a whole new level. 

Teach me! What other tips should I be using?  #travelhacks #sanfrancisco #wednesdaywomen

International Women’s Day sharing a date with Daylight Saving Time feels almost poetic.

A day about women.
A day with more light.

There are so many brave women I know who aren’t afraid to step into the light and just as many who aren’t afraid to /gently push/nudge/or shove, if necessary, another woman toward it.

Not every brave woman is the one at the center.

Sometimes she’s the one…
…making the intro.
…giving the endorsement.
…opening the door.
…sharing the opportunity.
…passing the mic.
… giving another woman that nudge to be seen.

That matters.

I’m grateful for the women I know who own their brilliance.

And I’m equally grateful for the women who see brilliance in someone else and refuse to let it stay hidden.

That kind of generosity can change careers, confidence, communities…all of it.

Take your turn shining in the spotlight or shine it on someone else. 

We need both. 💜

#InternationalWomensDay #WomenSupportingWomen #WomenInLeadership #WednesdayWomen

What did you do this week at work? I learned how to pitch better. You may be thinking, I don't sell anything. I don't need to know how to pitch. Well, I wholeheartedly disagree. 

I was lucky enough to host a Wednesday Women Members-Only Session with the iconic Precious L. Williams RainmakingSpeaker who talked with us about Positioning with Precision.  As you can tell, we were soooo bored and no one had any fun while learning sooooo much. 😉 

Here are a few bits of wisdom I took away from the call. 
Packaging is how you show up. 
Positioning is how the market perceives your value. 
Pitching is how you communicate that value to close. 

Everyone needs to know how to pitch well.

✅Job hunting - Pitching! 
✅Getting a raise or promotion - Definitely pitching. 
✅Talking to investors - They don't call it a "pitch deck" for no reason. 
✅Getting paid your worth to speak - Yep, still pitching. 
✅Sharing your business with a prospect - Well, duh! 
✅Getting your toddler to get dressed - You guessed it.
✅Asking your significant other to take out the trash - 😁 

So let's just say, we left with a lot of wisdom and fired up to implement it. 

But don't take it from me, I'm obviously biased. 

"Absolutely amazing session. I loved the energy and the information shared was on point. Thanks." 

"This was such a great lesson packed session - very practical, with tips I can and will implement immediately. Thank you Precious and WW."

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Leslie Greenwood

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The Battle

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