Alina Vandenberghe

Co-founder & co-Ceo @Chili Piper 🔥 🌶 Here I talk about lessons I learned to jumpstart my career from an intern to SVP. And to grow a company from 0 to almost 1 Bn

Started my own company before high school to pay for my own education. Sold lipstick and my tech skills. Decided to do a master in computer science because make-up was a low margin business

Went on to create first mobile products with millions of users for Thomson Reuters, Bloomberg, Pearson. Some of them went to be keynoted on stage by Steve Jobs 

The past ten years have got me back to entrepreneurship and it fits me like a glove. I founded Chili Piper - the demand conversion platform that doubles inbound conversion rates for cool companies like Spotify, Airbnb, Snapchat, Shopify and thousands others. Recently gone through a financial transaction that got us close to a billion dollar valuation 

On LinkedIn I write about lessons I learned as a woman & mom entrepreneur and hope to help others find their own giants within to prevail in their lives at work  

Co-Founder & Co-CEO

Chili Piper is the most advanced routing and scheduling software for B2B revenue teams. 
We solve interesting problems, live and breathe our core value of “help,” and have a ton of fun doing it while fully distributed around the world — powered by espresso and hot sauce. 


Want to join me in person in February in Florida for a workshop on building agentic workflows for marketing ? 

I will be hosting one of the workshops organized by Spiralyze  on February 10 in Fort Lauderdale 

I’ve been to Florida many times but never to Fort Lauderdale . I’m coming because I need some sun after all this snow in NYC but also because Sahil Patel  is a cool dude 

You can use code for a 50 % discount  ATFSPZ2 , this is the link https://lnkd.in/dSQ_dsn7

Alina Vandenberghe 🌶️

Co-founder & co-CEO @Chili Piper 🔥 Here I talk about lessons I learned to jumpstart my career from intern to SVP. And to grow a company from 0 to almost $1Bn

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

Huge favor to ask. I'm driving medical supplies into Ukraine later this year. And I need your help to fill the vehicle.


Through an organization called Convoy4Ukraine, I'll be purchasing a used 4x4, and loading it with tourniquets, trauma kits, generators, and warm clothing. 

I'll meet up with a handful of other volunteers doing the same thing (along with some mechanics for good measure), and we'll then drive these vehicles in a convoy from the UK, across Europe, and deliver it directly to Ukrainian families. 


These are people now entering their fourth winter without reliable heat or electricity. Not to mention the constant bombardment of drones and missiles to go along with that.


The vehicles don't come back. They stay in Ukraine for continued humanitarian use...evacuating civilians, delivering care packages to areas that have been destroyed, reaching elderly people who refuse to leave their homes despite the danger.


Also worth saying that these donations don't go into some random org where you hope it ends up in the right place. When we arrive in Ukraine, we'll hand off the vehicle directly to Ukrainian drivers. 

These are usually elderly men or young women...all of fighting-age men and women are at war.

Some of this aid goes to children in orphanages. Kids who didn't ask for - nor deserve - anything remotely like what they are going through now.


EVERY SINGLE DOLLAR raised will go into the purchasing the vehicle and supplies. As with any fundraiser, ANY dollar amount is game-changing.

I'm covering my own travel to/from Europe, and lodging during the 5-day drive, separately. This money needs to go exactly where it matters.


And if you can't donate, sharing this post could help reach people who can.


I'll be handing these supplies directly to families barely surviving a war they didn't ask for.

You can donate here: https://lnkd.in/gHDFP7E3

Really do appreciate your consideration on this, folks.

There's no such thing as a neutral interaction with a buyer. Every email, every call, every follow-up is either a deposit into your credibility account or a withdrawal. 

Those are the only two options.


Emily Leu introduced this concept during a Sales Assembly session yesterday, and I love how binary it is. There's no middle ground. No "that meeting was fine." No "we're in a holding pattern."

You're either building trust or you're eroding it. There is no fucking Switzerland.


Unfortunately, there are reps out there who think they're making deposits when they're actually bleeding credibility.


A few examples:


1. Sending a "just checking in" email? Withdrawal. You've signaled you have nothing valuable to offer.


2. Dodging a pricing question with "let me get back to you on that"? Withdrawal. Trust erodes immediately when you hedge.


3. Showing up to a demo late, camera off, scrambling to screen share? Withdrawal. You've communicated you're not fully present before saying a word.


4. Forwarding a 12-page case study PDF? Probably a withdrawal. Nobody's reading it. You've confused effort with value.



Here's what makes deposits:


1. Pricing transparency. 

"Here's how our pricing is structured. I'll need X, Y, and Z to give you specifics. Here's a ballpark so we know we're in range." 

Cards on the table. No games.



2. Trade-off honesty. 

"We're not the cheapest. We're not trying to be. Customers pick us when X and Y matter more than upfront cost." 

You're not hiding shit.



3. Competitive clarity. 

"What you'll see from them is heavy focus on this. That's not us. They're right for someone looking for A. We're right for someone looking for B." 

Framing trade-offs like a grown-up.



4. Micro-stories over case studies. 

A 30-second example of a customer who looks like them, what broke, and what changed. Sound bites > PDFs every time.



The thing about the credibility bank is that withdrawals compound faster than deposits.

One dodged question can undo three strong discovery calls. One "let me circle back" when you should know the answer makes them question everything else you've said.


So before every interaction, ask: deposit or withdrawal?


If you can't clearly answer "deposit," don't send it. Don't schedule it. Don't do it.

Your credibility balance is the only thing that makes everything else in your deal cycle work. 

And unlike actual banks, there's no overdraft protection.

Folks, if you sell into RevOps (or they are part of your buying committee), I have 3 pieces of advice for you:


First off, understand that RevOps doesn't give a shit about your features. They care about broken handoffs, dirty data, misaligned comp plans, and forecasting models that make their CEO question their competence. 

They live in operational hell every day, and they've sat through too many demos from reps who think "integration" means "we have an API."


If you want RevOps as an advocate, show up like a CONSULTANT, not a closer.


That means a few things:


1. Lead with diagnostic questions. 

Ask where reps are wasting the most time. Ask which part of the funnel has the lowest conversion and why they think that is. Ask how often they're re-forecasting and how far off it usually lands. 

You're trying to understand their system, not pitch your solution.



2. When you find the pain, make sure you're mapping to systemic problems.

RevOps doesn't lose sleep over one AE missing quota. They lose sleep over misaligned territories where three reps fight over the same accounts, overstuffed ICPs that let junk into the pipeline, and forecasting that's become just a guessing game.



3. If your solution fixes a systemic problem, prove it in their language. 

Not "our platform increases efficiency." Instead: 

- "Reduces admin time from 8 hours to 2 per week per rep." 
- Or "Improves qualification rate from 18% to 31%." 
- Or "Cuts cost per closed deal by $2,400." 

Focus on operational metrics they can defend to finance.



And look, keep in mind that RevOps rarely owns budget. They can identify the problem, evaluate solutions, and recommend a direction. But someone else signs the check.

So your job is to arm them to sell internally: 

- Build them a teardown deck showing current state versus future state. 
- Give them an ROI calculator that speaks finance language. 
- Create a change management timeline. 
- Draft internal comms they can use to announce the change. 
- Show them how you'll implement without disrupting Q2.


You're not trying to close RevOps, per se. You're trying to make them look like a hero to their leadership.


When you present to the CRO or CFO, position your RevOps contact as the one who identified the problem, evaluated the options, and drove the decision. You're just the tool they selected. 

If they get credit for the win, they'll fight harder to make it happen.


Don't just treat them as someone to validate integrations and bless the data model. That's why most reps get ghosted after the second call.

Show up like someone who understands the mess they live in. That's how you earn advocacy instead of silence.

If your retention is inconsistent, it might be because your CSMs are treating everyone the same.



A $500K strategic account and a $15K SMB customer have completely different needs, risks, and growth potential. You should set up three engagement models, not one:


1. Strategic Accounts - over $200K ARR.

These need a dedicated CSM handling max 15 accounts. Not 50. Not 30. Fifteen. 

Strategic accounts require bi-weekly executive business reviews where you're talking BOARD-LEVEL metrics. 

You're running quarterly strategy sessions with their C-suite. You're building custom success plans that map to their actual business outcomes. And you're doing proactive expansion planning with a 90-day rolling roadmap that identifies the next $100K before they even ask.


What does success look like here?

- Gross retention above 98%.
- Net retention north of 130%.
- Executive engagement scores hitting 8+ out of 10.
- Expansion pipeline at least 40% of base ARR.

Anything less means you're not treating them strategically...you're just keeping them happy.



2. Growth Accounts - $50K to $200K ARR.

These get pooled coverage where one CSM handles 30 to 40 accounts. Not strategic enough for dedicated resources, but too valuable for automation. 

- Monthly value reviews - and I mean actual value reviews, not "how's everything going" check-ins. 
- Quarterly expansion workshops where you're actively identifying upsell opportunities. 
- Semi-custom success plans tied to their company goals. 
- Automated health monitoring with manual intervention when scores drop.


Shoot for:

- Gross retention around 92%.
- Net retention targeting 115%.
- Product adoption scores above 75%.
- Expansion pipeline at 25% of base ARR.

You're their GROWTH partner on this, not their "strategic" partner. There's a difference. :)



3. Standard Accounts - under $50K ARR.

These should be 80% tech-touch with CSM intervention only for red flags. 

Quarterly webinars and group training instead of individual attention. Self-service resources and community support. Automated expansion nudges triggered by usage patterns, not manual outreach.


Success here can look like:

- Gross retention of 85%
- Net retention around 105%
- Support ticket resolution under 24 hours
- Self-service adoption above 70%

You're building efficiency at scale here. Less of a focus on building relationships.



When you segment like this, resource allocation finally matches revenue impact. Your best CSMs focus on the accounts that actually move the number instead of spreading thin across 80 random logos.

Don't stress about treating all customers the same. You don't have to be "fair."

Strategic accounts deserve strategic attention. Standard accounts deserve efficient support.

Segment your CS model or watch your best customers leave because they got the same treatment as everyone else.

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The Battle

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