Land and Expand: Win One Team, Then Win the Company

Land and expand wins small deals quickly, then grows within accounts over time. Starting small means faster sales cycles and lower risk; expansion happens as value is proven. In B2B SaaS, upselling costs $0.27 per dollar vs. $1.13 for new customer acquisition.¹ Atlassian, Slack, and Datadog turned single-team deployments into enterprise accounts.

What makes land and expand work is that it reduces initial deal risk and lets product value drive expansion. The product sells the expansion, not the sales team:

Expansion Paths

The key: land efficiently, expand relentlessly.

When land and expand works

Best Fit Products

Land and Expand Examples

Atlassian: 524 Customers Paying $1M+

524 customers paying $1M+. Growing 48% YoY. With just 12-21% S&M spend. Atlassian ($5.2B revenue, 20% YoY growth) proves what land-and-expand can achieve: 83% of Fortune 500 use their tools, and these enterprise deals started as small team deployments.²

How It Works

Lessons

1. Make landing frictionless with self-serve. Atlassian lets teams start without sales or approval, removing barriers to initial user adoption.
2. Deliver visible team value that spreads organically. Jira obviously helps engineering teams, and that success creates demand as other teams notice and want in.
3. Build cross-sell paths for expanded needs. Multiple products (Jira, Confluence, Jira Service Management) let usage grow through related needs, not just seat expansion.

Slack: Team → Department → Company

143% NRR through organizational expansion. Slack ($27.7B acquisition) grows account-by-account: one team starts, adjacent teams notice faster communication, the department adopts, the company standardizes. Teams hitting 2,000 messages signal expansion readiness.³

How It Works

Lessons

1. Make product success visible through viral mechanics. Slack spreads because you can’t use it without inviting others, and teams that use it work faster in ways others notice.
2. Build network effects that require expansion. Cross-team communication requires cross-team adoption, so more teams means more value for everyone.
3. Have enterprise tier ready when companies standardize. Compliance and SSO features let IT formalize what teams have already adopted organically.

Datadog: Multi-Product Expansion

140%+ NRR. 75% of new logos land with 2+ products. Time to value under 10 minutes. Datadog expands through product breadth: developers start with infrastructure monitoring, add APM, then logs, then more.⁴

How It Works

Lessons

1. Land with individual developers, not teams. Developer-first adoption means even lower friction than team-level entry.
2. Build a multi-product platform for adjacent needs. Datadog expands from infrastructure monitoring to APM to logs, capturing more use cases per customer.
3. Align pricing with usage growth. Usage-based pricing means revenue grows automatically as customers’ infrastructure scales.
4. Prove value fast. Under 10 minutes to value means developers can validate the product before anyone questions the adoption.

GitLab: 121% DBNRR Through Unified Motions

GitLab, the DevSecOps platform with an open-source Community Edition, achieves 121% DBNRR. Expansion is 80% from seat growth, plus tier upgrades. They generate 40% higher revenue per employee than sales-led peers by unifying product-led growth and enterprise under shared goals.⁵

How It Works

Lessons

1. Design for seat-based expansion. 80% of GitLab’s expansion comes from more users, so make adding seats frictionless and valuable.
2. Unify PLG and sales on shared metrics. GitLab aligned both motions on new logo and ARR goals, eliminating internal competition.
3. Create clear tier progression. Community to Premium to Ultimate gives customers a visible upgrade path as needs grow.
4. Build trust through open source. Developers adopt before procurement gets involved, creating bottom-up demand.

Segment: $3.2B Acquisition via Developer Expansion

One SDK integration. Then another data source. Then analytics, marketing tools, and warehouses. Segment ($3.2B Twilio acquisition) grew 150% ARR over two years by letting developers start small and expand into company-wide data infrastructure.⁶

How It Works

Lessons

1. Land with one use case, not full infrastructure. A single SDK integration takes minutes, proving value before anyone commits to broader adoption.
2. Expand through connections that deepen dependency. Each new source or destination makes Segment more valuable and harder to remove.
3. Target developers before data teams get involved. Developer-first adoption bypasses slower procurement processes.
4. Add sales for expansion, not landing. Self-serve handles adoption; sales helps customers expand once they’ve proven initial value.

1Password: Consumer to Enterprise Expansion

180K+ business customers, largely sourced from 1M+ individual developers. 1Password ($6.8B valuation, $400M+ ARR) shows how personal adoption feeds enterprise: when individuals love the product at home, they bring it to work. Family plans create multiple advocates per account.⁷

How It Works

Lessons

1. Start consumer to create professional advocates. Personal use builds familiarity, and individuals bring the tools they trust to work.
2. Use family plans as a multiplier. Multiple users per account means multiple potential champions who might advocate for business adoption.
3. Design for work/personal crossover. When the same tool works in both contexts, expansion from consumer to enterprise happens naturally.
4. Let compliance needs trigger tier upgrades. Enterprise security requirements give IT a reason to formalize and expand organic adoption.

Asana: PLG + Enterprise = $600M ARR

Product-led growth doesn’t automatically mean efficient go-to-market. Asana ($600M+ ARR, 34% growth) proves the point: enterprise NRR is 135%, and $100K+ customers grew 80% YoY, but S&M spend is 62% of revenue. Land and expand works. PLG efficiency isn’t guaranteed.⁸

How It Works

Lessons

1. Land free, expand enterprise. Freemium lets small teams succeed without company buy-in; sales helps convert them into $100K+ deals.
2. Watch S&M ratios closely. Product-led growth should improve efficiency, not mask it. Asana’s 62% S&M spend shows that bottoms-up adoption doesn’t guarantee efficient go-to-market.
3. Focus on your highest NRR segment. Enterprise customers deliver 135% NRR vs. lower rates for SMB. Know which segment drives expansion.
4. Use community feedback to drive product. Asana’s product-led foundation since 2008 means user input shapes the roadmap, creating better retention.

Product Success Drives Account Expansion

Sales didn’t convince the second team to adopt. The first team’s success did. 143% NRR happens when expansion is product-driven, not rep-driven. The “land” proves value; the “expand” follows automatically.

Action Items

1. Test your landing friction: Can a single team start using your product without a sales call, IT approval, or budget sign-off? Try it yourself with a new email. If you need to “contact sales,” you’re not doing land and expand. You’re doing enterprise sales with small deals.
2. Calculate your expansion contribution: What percentage of new ARR this quarter came from existing accounts vs. new logos? If it’s below 30%, your “land” isn’t leading to “expand.” Either your product doesn’t spread, or you’re not tracking it.
3. Find your expansion signal: What behavior predicts an account is about to grow? Slack uses 2,000 messages. Datadog uses multi-product adoption. Pull your last 20 expansions. What did they have in common 30 days before they expanded? That’s your PQL trigger.
4. Interview your biggest expansion: Call the account that grew the most last quarter. Ask: “How did you go from one team to company-wide?” The answer reveals your actual expansion motion, which may differ from what you think it is.
5. Measure land-to-expand velocity: How long from first team signup to second team? How long from second team to enterprise deal? If teams land and stay small for 12+ months, you don’t have land and expand. You have small deals that stay small.