Can a company build a PLG motion and an enterprise sales motion at the same time, or must it sequence them?

Harry Stebbings · Jun 7, 2023

Starting bottoms-up is easier because a PLG org has an inherent product-and-growth-first mindset that is very difficult to instill in an enterprise org later, whereas bolting enterprise sales onto a PLG motion is easier than people assume.

The product-first mindset is hard to imbue after the fact, while the right sales leader can add an enterprise motion on top of PLG effectively.

Scope: assumes you hire a strong enterprise sales leader

24:12 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Kevin Egan · Jul 12, 2023 · hedged

Pursuing PLG and enterprise simultaneously is possible but extremely difficult; the better path is sequential — PLG first to build end-user love, then layer on enterprise.

Capturing end-user love is one thing, but building the enterprise security feature set, processes and controls needed to go big in enterprise takes many years.

Scope: Slack managed to do both, nailing PLG first while always keeping an eye on enterprise; 'if I had to pick a path'

7:56 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Matt Rosenberg · Oct 4, 2023

Enterprise is a fundamentally different business from product-led growth — language, messaging, positioning, customers, product, pricing and staffing all differ

He has built enterprise motions on top of PLG twice, at Eventbrite and Grammarly, and everything about the two motions differs

Scope: hard but achievable; the two motions must be reconciled so they don't cannibalize or conflict

41:13 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Geoff Charles · Dec 6, 2023

New products should be launched at the bottom of the market via product-led growth with no sales and little marketing, then handed to a small sales team once positioning and ICP are proven

PLG at the low end proves the business case and lets you iterate until you can show the sales team the positioning, use case, ICP and revenue potential before scaling

Scope: describes how Ramp has done it

24:59 20VC: Ramp's Product Playbook: How To Hire Product Teams, How to Run Sprints, How to Increase Product Velocity, When and How to Go Multi-Product with Geoff Charles, VP Product @ Ramp

Harry Stebbings · Sep 18, 2024

A company that wants to build enterprise must eventually build outbound and a real enterprise function rather than continuing to rely on product-driven inbound.

Scope: applies to companies with enterprise ambitions

16:09 20VC: Notion's Founder on "Founder Mode": When it Works & When it Doesn't | Why The Way Startups Fundraise & Construct Boards is Broken | Raising at a $10BN Valuation in Peak Bubble Times and How Notion Has More Money Than Ever Before with Akshay Kothari

Jake Saper · Mar 10, 2025

All product-led-growth companies eventually need to layer an enterprise sales motion on top of PLG to be sustainable and enduring

Bottoms-up PLG alone doesn't make a business enduring; Zoom's technical founder needed help building the enterprise motion and that commitment is why Emergence won the deal

8:33 20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital

Ron Gabrisko · Aug 4, 2025

The biggest early-stage sales mistake is founders handing sales off to their first salesperson instead of staying involved until roughly $5-10M ARR

No one is more passionate about selling the product than the founder, and founder-led selling is how you hear about your product; a salesperson can get it wrong and set you back at least twelve months

Scope: Until you know what people are buying and can write a first playbook

23:50 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Shaunt Voskanian · Mar 21, 2026

Figma's sales motion has shifted from almost exclusively upgrading existing self-serve customers to higher tiers, to a largely sales-led motion in mid-market and above

existing customers think they're happy and have figured out one way to use Figma, so reps approach them with proactive insights drawn from patterns across other customers

Scope: mid-market and above; outbound into existing customer base, not cold prospects

7:16 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Lauren Schwartz · Oct 19, 2022

For an enterprise product, only an enterprise sales team can create recognition across a whole enterprise, so top-down sales combined with product-led growth is what truly drives momentum.

A first deal with a big logo is a very narrow land — a couple of users isn't the end of the job — so PLG alone can't expand wall to wall.

Scope: for enterprise products; some companies can succeed with a sales-led motion alone

11:36 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Kevin Egan · Jul 12, 2023

Slack's marrying of end-user love with an enterprise posture and large-team focus from day one was unique at the time and drove its hypergrowth.

Slack's value increases with the size of the team on the platform, so it had an appetite for large customers from the start while remaining highly engaging.

5:44 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Luke Harries · May 23, 2025

Companies should run top-down enterprise marketing and bottoms-up developer marketing as separate teams with different goals rather than choosing one motion

The audiences roughly overlap, so both motions work in tandem and you can grow quickly while landing the best companies

Scope: assumes you want to grow super quickly and work with the largest companies

39:41 20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries

Ron Gabrisko · Aug 4, 2025

You can run an SMB/digital-native segment and an enterprise segment simultaneously rather than abandoning one

At Databricks a dedicated first-line leader kept SMB/digital natives generating revenue while the enterprise segment was built out

Scope: 'It's a handful'; Requires a separate leader for each segment

21:11 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Aaron Levie · Apr 20, 2026

PLG motions and forward-deployed enterprise services models are not mutually exclusive

29:49 20VC: Everyone is Wrong; We Will Have More Developers in Five Years | Why Frontier Labs Will Be Way More Valuable Than They Are Today | Are SaaS Companies Cooked: Which Thrive & Which Die with Aaron Levie, Founder at Box

Stevie Case · Jan 25, 2023

Startups should avoid running PLG and enterprise sales motions simultaneously from day one

Combining them confuses customers and gets sales teams tangled in credit and comp mechanics — who gets credit when someone self-signs up but a rep closes the deal — so going at commercialization from two angles makes everything messy

Scope: it is technically possible, just cautioned against; early days of sales specifically

12:19 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Harry Stebbings · Jun 7, 2023

Doing PLG and enterprise sales at the same time is a massive mistake

Companies do it because they're too nervous to commit and burn the boats on either motion

20:42 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Rich Liu · Jun 7, 2023

It is very hard for a company to do PLG and enterprise well at the same time; you should commit to one motion and evolve to the other later.

The two motions require fundamentally different product architecture, engineering DNA, marketing (consumer vs multi-touch attribution lead gen), and go-to-market muscles, so doing both well requires commitment, DNA and resourcing most companies don't have.

Scope: defines enterprise as $100k+ deals with 6-12 month cycles and PLG as pure self-serve; acknowledges a middle 'velocity/sales-assist' motion exists; okay to evolve to the other motion later, just not too early

21:02 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Harry Stebbings · Nov 29, 2023 · hedged

Startups can't run PLG and enterprise motions well at the same time and should focus on one before moving to the other over three to five years

Scope: stated as his standing advice to startups, offered up for challenge

8:34 20Growth: The Golden Rule to $100M in ARR, Why CAC to LTV is BS Early On, Why Your First Growth Hire Should Be a Former Founder & How Ramp Does 200 Growth Experiments Per Quarter with Guillaume Cabane

Matt Rosenberg · Oct 4, 2023

You don't need to run an enterprise pilot — the test already happened organically and the signal sits in your existing usage data

PLG products are already deployed in enterprise-like ways (large orgs on Eventbrite; 3,000 of Compass's 30,000 employees using Grammarly), because people bring their applications to work

Scope: it doesn't mean the product is optimized for that environment; doesn't mean it always should be used there

43:42 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Martin Gontovnikas · Feb 14, 2024

Most companies wrongly treat top-down sales as a separate silo from PLG; top-down should instead be run off bottoms-up signal — outbound to directors and VPs of engineering/product at companies where a developer has already signed up

Outbound into a warm account where someone is already using the product beats cold outbound to a company that has never heard of you

32:50 20Growth: How to Master Product-Led-Growth, The Biggest Mistakes Startups Make When Scaling into Enterprise, How to Assess "Bets" in Growth; Which to Take and Which to Not with Gonto, Interim CMO @ Vercel

Guillaume Cabane · Nov 29, 2023

It is very rare for an early-stage company to have one of the two motions (PLG or enterprise) pinned down; most try a bit of both and land in between, running both motions for efficiency reasons

They optimize for efficient acquisition and selling on CAC grounds, and that naturally lands them with both motions

Scope: early stage

8:55 20Growth: The Golden Rule to $100M in ARR, Why CAC to LTV is BS Early On, Why Your First Growth Hire Should Be a Former Founder & How Ramp Does 200 Growth Experiments Per Quarter with Guillaume Cabane

Guillaume Cabane · Nov 29, 2023

Companies usually end up in a dual motion insidiously rather than by choice: they start in SMB, a risk-tolerant enterprise buyer offers 3-5x their ACV, they take it, and then must layer on cost structure to prevent churn and keep the logo

You can't refuse a deal at multiples of your ACV, and once you have the logo on your site and in your board deck you have to support it so it doesn't churn

Scope: typical path, not universal

11:47 20Growth: The Golden Rule to $100M in ARR, Why CAC to LTV is BS Early On, Why Your First Growth Hire Should Be a Former Founder & How Ramp Does 200 Growth Experiments Per Quarter with Guillaume Cabane

Kim Graves · Jun 27, 2025

PLG companies should start building outbound earlier than they think — typically after the first three or four 'Renaissance reps' are onboard

Upmarket buyers won't buy without talking to a human, Fortune 100 executives aren't tinkering with new tools so you can't reach them via a product-led motion, and outbound takes about a year to figure out (which accounts, who inside them cares, what messaging books meetings)

Scope: assumes an upmarket/enterprise ambition

44:23 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Chris Degnan · May 23, 2026

The best go-to-market model is to build an outbound, sales-led growth engine first and layer PLG on top of it

PLG-only companies produce order takers; great outbound go-to-market people are what differentiate a company

5:41 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Ishan Mukherjee · Apr 4, 2025

Early-stage companies should not attempt PLG and enterprise sales simultaneously unless they have a single leader who deeply understands engineering, product, sales and support and manages the funnel daily

Without a singular figure who understands the whole motion, the effort fragments into two or three siloed organizations that don't work together

5:00 Only with one leader owning the whole funnel

John McMahon · Nov 28, 2025

Companies fall into a 'PLG trap': having built cost model, people and culture entirely around PLG, they cannot make the move to enterprise when they need bigger deals and hit a wall

Moving upmarket requires hiring $300k-OTE enterprise reps, changing the cost model, the people and the go-to-market, which PLG-native organisations can't execute

59:14 Plg cost model and culture block later enterprise move

Chad Peets · Aug 23, 2024

PLG and enterprise sales are entirely different motions, and nailing one does not make you more likely to nail the other

A low-level developer swiping a credit card is a completely different value proposition from selling to a CTO, who likely doesn't care that engineers use the product; enterprise is driven by a go-to-market function while PLG is driven by the product

47:51 Motions are distinct skills success does not transfer

Harry Stebbings · Aug 23, 2024

One of the biggest mistakes founders make is expanding into enterprise too early on the basis of being 'pulled' there

At a few million in ARR a company doesn't need to be pulled anywhere

49:03 Customer pull is not a valid trigger enterprise too early

Chad Peets · Aug 23, 2024

Companies should deliberately start in mid-market and move upstream to enterprise later

Smaller accounts have lower demands, so you can nail a small set of customers, make them very happy, and learn what the enterprise will require while building the product out

49:17 Start mid market then move upstream

Anton Osika · Aug 18, 2025

Lovable will build an enterprise sales team but will not become an enterprise company; its enterprise sales function is about talking to and understanding customers and giving them the tools to get value, not top-down hustling and wining-and-dining CEOs

Enterprise selling for Lovable is a customer-understanding and enablement function, so it doesn't worry him the way classic top-down enterprise sales would

50:44 Enterprise function as customer understanding not top down hustling

Guillaume Cabane · Nov 29, 2023

Enterprise-first companies cannot successfully pivot to adding a PLG motion

The acquisition doesn't work and the product isn't self-serve — you can't retrofit self-serve onto software designed for CSMs to configure the instance

10:32 Enterprise first companies cannot retrofit a plg motion

Guillaume Cabane · Nov 29, 2023

Opening a second motion does cost you something, because startup success is focus — the ability to concentrate effort so you grow faster than competitors

If you lose focus, competitors grow faster than you and you lose

11:20 Running a second gtm motion costs focus and competitive speed

Shiv Rao · May 16, 2026

The standard investor advice to start downmarket and swim upstream is only partly right in healthcare, because US healthcare is not one trillion-dollar market but many segmented markets

Who you serve determines segmentation; if you serve clinicians, most of the ~800,000 practicing doctors are concentrated in large integrated delivery networks, payer-providers and academic medical centers

12:48 Buyer concentration not company size sets the entry point

Stevie Case · Jan 25, 2023

The right time to add salespeople to a PLG motion is when you can test that a human in the relationship drives more revenue while the customer is also happier and solves a problem automation can't

If adding the human experience to the product experience produces a better combined outcome, that's the signal; you learn this only by experimenting

13:38 Experimentally test whether human touch improves revenue and satisfaction signals readiness

Stevie Case · Jan 25, 2023

An upmarket experiment requires dedicated people working 100% on the new segment, not existing reps dipping a toe

It's very hard for one person to do both high-velocity bottom-of-market deals and strategic deals; they will always default to whatever produces the best revenue and comp results and whatever they already know how to do

17:02 Dedicated full time team not part time reps tests the new motion

Guy Podjarny · May 24, 2023 · hedged

PLG startups can shift messaging toward productivity and cost savings in this environment, but risk being lured onto an enterprise path when their market is really best served by product-led motion

Acknowledging the current buying reality is necessary, but the enterprise path may not fit the market's natural shape, so it has to be a case-by-case decision

25:59 Macro pressure tempts plg companies into a premature enterprise shift even when plg fits better

Kevin Egan · Jul 12, 2023

The signal that it's time to move into enterprise is being pulled there by customers — user counts grow large enough inside companies that procurement and legal come to the table wanting proper terms.

If the product is generating real end-user value and spreading virally within companies, those companies will demand you operate as a strategic partner rather than a rogue service; this is what happened at Slack with tens of thousands of users in single accounts.

8:45 Customer pull triggers the enterprise layer

Howie Liu · Aug 25, 2023

The hardest part of the PLG-to-enterprise transition is product/go-to-market alignment: a product whose value is experienced only by individuals is very hard to sell to a senior enterprise buyer.

Without team or org-wide value that is more than the sum of its parts, you are forced into a productivity sale, which is increasingly weak in an environment where enterprises are consolidating thousands of SaaS tools to reduce vendor relationships and internal support burden.

18:14 Product must deliver team or org wide value not just individual value to sell upmarket

Rich Liu · Jun 7, 2023

Which motion to start with depends on your market and team DNA: enterprise security should start top-down where the need is biggest, while an online ads business should go bottoms-up.

The inherent need and buyer profile differ by category, so the natural entry point differs.

23:43 Depends on market need and team dna

Rich Liu · Jun 7, 2023 · hedged

Adding an enterprise motion on top of PLG works only if you don't get ahead of where the product, customer success and services orgs are ready.

24:32 Enterprise layer gated by product and cs readiness

Matt Rosenberg · Oct 4, 2023

The right time to start the enterprise motion is when you have control and visibility over the PLG motion — not when it's perfected

You'll never feel great about it; once you know which dials to turn on acquisition spend and retention, that's enough control to start the other side

42:49 Control over plg dials is the trigger