Moving Upmarket and Serving Multiple Segments

If you’ve grown a SaaS or fintech product from scrappy beginnings, you eventually hit the same fork in the road:
keep living in the cozy world of small customers, or move upmarket into bigger, messier, more lucrative deals.
That’s the leap Square made evolving from a scrappy payments dongle for micro-merchants into a global platform
serving everyone from weekend market stalls to complex, multi-location retailers.

On SaaStr Podcast 478, Square’s Global Head of Sales walks through how they moved upmarket while still serving
multiple customer segments at once. In this article, we’ll unpack those lessons, layer in additional insights
from top SaaS and go-to-market thinkers, and turn the episode into a practical playbook you can steal.

What “Moving Upmarket” Really Means (Spoiler: It’s Not Just Raising Prices)

Many founders secretly translate “moving upmarket” as “charging more and adding the word enterprise to the
pricing page.” If only.

In reality, moving upmarket means intentionally shifting more of your revenue toward mid-market and enterprise
customers organizations with more users, more complexity, more stakeholders, and far longer buying cycles.
You’re not just asking for bigger checks; you’re signing up to solve bigger problems and survive more scrutiny.

From micro-merchants to multi-location sellers

Square’s story is a classic example. They began by serving micro-merchants: food trucks, pop-up stalls, solo
service providers. Those customers bought fast, churned sometimes, and needed simple, intuitive tools. Over
time, Square layered in:

Full point-of-sale systems for restaurants and retailers
Online stores and invoicing tools
Inventory, payroll, and team management
Lending and other financial services

The same core idea helping sellers get paid and run their business scaled from a single person at a market
booth to chains with multiple locations, staff, and complex operations. That’s moving upmarket done right:
expanding the size and complexity of customers while staying anchored in the
same fundamental job you’re hired to do.

The Jobs to Be Done Lens: Square’s Secret Weapon

A big theme in the SaaStr conversation is the “Jobs to Be Done” (JTBD) framework. Instead of obsessing over
features, Square focuses on the job a customer is trying to get done when they “hire” the product.

Step 1: Name the core job

For Square’s earliest customers, the job sounded something like:
“Help me take card payments anywhere so I don’t lose sales.”
Simple, clear, and incredibly powerful. As they moved upmarket, the job got richer:
“Help me run a unified, omnichannel business across in-store, online, and mobile without losing my mind.”

Your first task: describe your customer’s job in one sentence, in their language. If that one sentence doesn’t
make a bigger, more complex customer nod and say “yep, that’s my life,” you’re not ready to move upmarket yet.

Step 2: Ask if that job exists in other segments

JTBD is powerful because it travels. Once you define the core job, ask:

Does this same job exist in larger companies?
Do they experience the pain more often, more expensively, or more visibly?
What extra constraints (compliance, security, workflows) show up at their scale?

Square realized that “run a modern, connected business” is a job shared by tiny merchants
and large retailers but the larger sellers needed stronger reporting, more integrations,
multi-location controls, and sophisticated permissions. Same job, new requirements.

Step 3: Use JTBD to guide product, packaging, and messaging

Instead of inventing entirely new products for every new segment, Square treated moving upmarket as a
packaging and experience problem. Which capabilities are table stakes? Which become “pro”
or “enterprise”? Which are only meaningful when a company has multiple locations or teams?

When you think in jobs instead of features, it becomes easier to:

Simplify the entry-level product for smaller customers
Expose more power, control, and customization to larger customers
Craft messaging that speaks directly to the outcome, not the feature checklist

Serving Multiple Segments at Once Without Losing Your Mind

The hardest part isn’t just moving upmarket it’s doing that while keeping your original SMB base healthy.
Square didn’t abandon micro-merchants when they started winning larger deals. They learned how to segment
intelligently and run different motions in parallel.

Segment by size, complexity, and value

Most SaaS companies ultimately land on a segmentation model that looks roughly like:

SMB: self-serve or low-touch sales, simpler needs, high volume
Mid-market: mix of self-serve and sales-assisted, moderate complexity
Enterprise: full sales cycle, many stakeholders, long deals, big ACVs

But the best teams don’t stop at company size. They also look at:

Vertical (retail, restaurants, services, healthcare, etc.)
Channel (online only vs in-person vs omnichannel)
Expansion potential and LTV
Support intensity and implementation complexity

Square’s world is naturally segmented by seller type: coffee shop, salon, retail store, restaurant, and so on.
Each of those segments exists at multiple sizes, from one-location shops to regional chains. That’s a perfect
case for multi-segment strategy: similar workflows, different scale.

Design different motions for different segments

Trying to sell to a solo freelancer and a 500-location retailer with the same process is like trying to wear the
same outfit to the gym and a wedding. Possible, but not advised.

A practical pattern inspired by Square and other successful upmarket players:

SMB: Product-led growth, free trials, self-serve onboarding, light-touch sales or chat-based reps.
Mid-market: Inbound plus targeted outbound, discovery-heavy demos, advisory selling, basic implementation help.
Enterprise: Dedicated account executives, solutions engineers, proof-of-concepts, procurement and security reviews, executive sponsors.

The product may be largely the same, but the way you sell, price, and support it changes dramatically.

Pricing and Packaging When You Go Upmarket

Bigger customers come with bigger expectations, especially around pricing and packaging. The SaaStr conversation
emphasizes that you should think of moving upmarket as a packaging exercise first, not just
a pricing change.

From one-size-fits-all to tiered value

A classic evolution goes like this:

You start with one simple plan to keep things easy.
You add Good / Better / Best tiers as the product grows.
You introduce an enterprise tier with usage-based or custom pricing.

The key is to align tiers with the job and the segment:

SMBs care about ease of use, speed to value, and predictable costs.
Mid-market companies want flexibility, integrations, and reasonable control.
Enterprises insist on security, compliance, support SLAs, and customization.

Your packaging should make that progression obvious. If your smallest plan includes everything under the sun,
you leave no room to grow. If your enterprise plan is just “call us,” you haven’t really thought through what
the largest customers actually value.

A word on discounting and contracts

Upmarket deals often involve:

Annual or multi-year contracts rather than month-to-month
Volume-based pricing and minimum commitments
Co-marketing, pilots, and phased rollouts

Square and similar companies get leverage by anchoring discounts to commitment and expansion: better pricing
in exchange for more locations, more terminals, or longer terms. The goal is not to slash prices, but to align
incentives so everyone wins over the long term.

Building a Sales and GTM Team for Multiple Segments

One of the most practical parts of the SaaStr episode is how Square structures its teams. You can’t serve
wildly different customers with a single generic sales team and hope for the best.

Hire for the segment, not just the logo

Selling to a boutique retailer is a different career than selling into a Fortune 500 chain. Enterprise sellers
are used to navigating procurement, legal, and security reviews. SMB sellers thrive on velocity and volume.

Square’s global sales leadership emphasizes hiring people who already speak the “language” of the segment
you’re moving into whether that’s a particular vertical (restaurants, healthcare, retail) or a maturity level
(mid-market vs enterprise). That speeds up trust and shortens the learning curve.

Tight feedback loops with product and marketing

When you serve multiple segments, feedback gets noisy fast. That’s why the episode highlights the importance of:

Regular meetings between frontline sales, support, and product
Clear ways to tag feedback by segment and vertical
Joint planning between sales and marketing around new segments

If your product team hears “customers want X” without segment context, you’ll end up building features for the
loudest voice, not the most strategic customer.

Common Mistakes When Moving Upmarket

The SaaStr conversation, plus insights from investors and operators who’ve seen this movie before, surface a few
consistent mistakes:

1. Abandoning your SMB base too early

Upmarket ACVs are seductive, but your SMB customers are often your laboratory, your brand advocates, and your
training ground for product-led growth. Square never stopped serving micro-merchants; they expanded around them.

2. Trying to rebuild the product from scratch

If you feel like you need a completely different product for enterprise, you probably picked the wrong segment
or you don’t yet understand the core job. The strongest upmarket stories keep the same product DNA but make it
more configurable, integrated, and robust.

3. Underestimating complexity and sales cycle length

Bigger deals mean more stakeholders, more security reviews, more legal redlines, and more “let’s revisit this
next quarter” emails. If you don’t adjust your pipeline math, you’ll think the sky is falling when in reality
your sales cycles just got longer.

4. Overcomplicating your org chart

Some companies respond to upmarket ambition by spinning up a new “enterprise” group that fights constantly
with the SMB team. Square’s example shows you need clear swim lanes but also shared goals and leadership
that can arbitrate conflicts and keep everyone focused on total company health, not just one segment.

How to Apply Square’s Lessons to Your Own Company

Let’s turn this into a practical, step-by-step playbook you can use, even if you don’t have “Global Head of
Sales” in your title (yet).

Step 1: Define and validate your core job

Write down your main customer job in one sentence.
Validate it with real customers in different segments.
Check whether larger companies feel the same pain, just at higher stakes.

Step 2: Choose one or two adjacent upmarket segments

Don’t try to jump straight from tiny startups to global enterprises.
Pick a logical next segment: for example, from small retail to regional chains, or from small agencies to larger firms.
Assess what needs to change in product, support, and pricing to serve them well.

Step 3: Tune pricing and packaging

Align tiers to segment complexity, not random feature bundles.
Make the path from SMB to mid-market and enterprise visible and intuitive.
Experiment with pilots, usage-based add-ons, and multi-year incentives.

Step 4: Align GTM and hiring

Decide who owns which segment and document it.
Hire or reassign reps who have lived in the segment you’re targeting.
Set different success metrics for SMB vs mid-market vs enterprise reps.

Step 5: Build feedback loops across segments

Tag feedback by segment so product and leadership can prioritize clearly.
Review deals won and lost in each segment every quarter.
Use those insights to refine JTBD definitions, pricing, and messaging.

Real-World Experiences: What Moving Upmarket Feels Like on the Ground

Theory is nice, but moving upmarket and serving multiple segments is lived in messy calendars, Slack threads,
and “can you join this customer call in 5 minutes?” messages. Here are some composite, real-world experiences
inspired by what Square and other SaaS companies have gone through.

Experience 1: The first big logo… that breaks your processes

Picture a payments startup that has grown steadily with small retailers. One day, a regional 80-location chain
wants to rip and replace their legacy system. The team is ecstatic. Then reality hits.

The chain needs:

Custom user permissions for regional managers
Single sign-on with their existing identity provider
Rollouts staged by region, not all at once
Training sessions for hundreds of employees

None of those requirements existed in the SMB world. The startup scrambles: engineers accelerate an admin
permissions overhaul, customer success becomes an impromptu training team, and sales learns to navigate
procurement. It’s chaotic, but the result is a more robust platform that also benefits mid-market customers.
This is exactly the sort of stress test Square faced as they started working with larger sellers: the first big
customers expose all the seams in your product and processes and that’s a good thing if you choose to learn
from it.

Experience 2: The SMB team vs. Enterprise team tug-of-war

As companies add enterprise reps, a familiar conflict emerges. Enterprise asks for highly specialized roadmap
items to close a handful of huge deals. The SMB team worries those changes will clutter the product and confuse
smaller customers.

Mature organizations solve this by putting the job to be done at the center of the discussion.
Any enterprise request must either:

Strengthen the core job in a way that still works for SMBs, or
Be safely tucked behind configuration, roles, or advanced settings.

Square’s focus on packaging instead of separate products reflects this mindset. Rather than building a “Square
Enterprise” that only big brands can use, they enhanced the platform so larger sellers can turn on more control
and complexity when needed while smaller merchants still enjoy simplicity by default.

Experience 3: Learning to say no to the wrong “enterprise” deals

Another lesson that comes up repeatedly in conversations with operators: not every big logo is worth chasing.
Some “enterprise” prospects want deep custom work that pulls you away from your core job and stretches your
roadmap beyond recognition.

Smart teams create a simple checklist before pursuing big opportunities:

Does this customer’s core job match the job we already serve?
Will requested features benefit many customers, or just this one?
Will this deal meaningfully deepen our presence in a strategic vertical?

When the answer is “no” across the board, the bravest move is to walk away, even if the potential contract
value makes your eyes light up. Square’s ability to stay anchored in their mission helping sellers of all
sizes run and grow their businesses is a big part of why their upmarket motion didn’t turn into a bespoke
consulting shop for giant brands.

Experience 4: The moment the segments start feeding each other

Done right, serving multiple segments creates a flywheel:

SMBs provide volume, brand reach, and fast feedback on product changes.
Mid-market customers validate that the platform can handle more complexity.
Enterprises bring scale, credibility, and resources for deeper integrations.

Over time, features built for enterprise stability (better reporting, stronger uptime, advanced permissions)
improve the experience for mid-market and even some SMBs. Meanwhile, the usability demanded by smaller
customers keeps the product from becoming a bloated, consultant-only beast. This balance is visible in how
Square’s tools remain approachable for a solo shop owner, yet powerful enough for multi-location sellers with
complex workflows.

That’s the real promise of moving upmarket and serving multiple segments at once: not just bigger deals, but a
stronger, more resilient product and business.

Key Takeaways from Square’s Journey and SaaStr Podcast 478

Moving upmarket is one of the most important transitions a SaaS or fintech company can make and one of the
easiest to botch. Square’s Global Head of Sales highlights a few enduring truths:

Anchor everything in the customer’s job to be done.
Think of upmarket moves as packaging and GTM problems, not purely pricing changes.
Segment intelligently and design distinct motions for SMB, mid-market, and enterprise.
Hire people who know the space you’re entering and give them clear swim lanes.
Keep tight feedback loops so you can learn fast without losing your original base.

If you can do those things, you don’t have to choose between being loved by small customers and respected by
big ones. Like Square, you can become the platform that scales with your customers from their very first
swipe to their hundredth store.