How an ex-lawyer & an ex-Palantir engineer grew Ironclad into a $3.2 billion unicorn in 9 years.
Episode 97
Friends,
In 2014, Jason Boehmig and Cai GoGwilt founded Ironclad with a clear mission: to bring contracts into the digital age.
Their complementary backgrounds made for the perfect combination.
Jason was a former corporate attorney at law firm Fenwick & West who had experienced firsthand the inefficiencies of legal paperwork. Before that, he worked as a bond trader at Lehman Brothers, where he saw how tech could transform routine financial processes at scale.
Cai on the other hand, brought technical expertise as an MIT graduate in Computer Science and Physics and was a former software engineer at Palantir. At the time, he was looking to explore how to apply software collaboration principles to a new domain.
Both Jason & Cai met at a legal tech conference in October 2014, discovered they had complementary skills and a shared vision, and decided to team up. They both realized that contracts with version control issues, multi-party collaboration, and repetitive tasks – resembled a system that could be “coded” better.
The both of them founded Ironclad within a month of meeting, convinced that “business contracts in 2014 were as inefficient as shipping before containerization”, ripe for a new solution.
Today they are valued at $3.2 billion and are a leader in the contract lifecycle space. Here’s how they got here:
Brought to you by:
Market Curve is a premium tech storytelling studio run by me Shounak that turns tech companies into media companies. I’ve had the fortune of working with some of the top tech companies backed by some of the top investors like YCombinator, 20VC who have gone on to be acquired by companies like Roblox & Amplitude.
I’ve also helped founders grow their personal brand in the v0 stage, while writing essays that go viral on social media for companies closer to the PMF spectrum.
Here are a few things I can help you with —
Longform blogs, essays, and newsletters that drive authority.
Web & landing page copy that converts.
Ghostwriting for busy founders & execs who want to stand out.
Want to turn your startup into a media company?
Early MVP & Validation:
The founders immediately looked to validate the idea with real users. They quit their jobs and joined Y Combinator’s accelerator in Summer 2015.
Ironclad's MVP was the textbook definition of doing things that don't scale.The first version wasn't software as a service at all. It was Jason as the backend.
Ironclad's earliest customer acquisition was remarkably straightforward. Jason would pitch his concept to virtually anyone he encountered, asking, "Do you have contracts and would you like help with your contracts?"
Their first paying customer came from a personal connection at a friend's event. From there, they secured additional clients through persistent outreach and rapid response to customer needs. For example, this one time, they built an entire repository feature during a train ride from San Francisco to San Jose to meet a prospect's requirements. Talk about hustle!
"It's wild to think back to this now that we're in the AI assistant boom because the first version of Ironclad was an automated assistant for legal paperwork - but it was really me on the backend of an email address," - Jason Boehmig
The product workflow was made deliberately simple. Users would email admin@ironclad.ai with requests like "Hey, I'm doing an NDA with Joe Smith. Can you help us get it done?" Boehmig would manually respond with templates and guidance, mimicking what would later become automated features. Meanwhile, Cai observed this process, identifying patterns and gradually automating repetitive tasks.
For two years, they had one goal: be the BEST contract platform in SoMa (that was their local district in San Francisco). As a result, on-site meetings became 10x more valuable, meetings were on-site by default, they could provide extreme levels of customer support is an unfair advantage vs. competitors.
Ironclad’s strategy for acquiring its first customers was very much land-and-expand: land a team within a tech company (often the legal or sales ops team) by solving their immediate contract pains (like speeding up vendor agreements or offer letters), then expand usage to more contract types and departments.
This approach allowed them to validate their concept while building trust with early users. It also provided invaluable insights into user needs that informed their product development roadmap. They were also careful to fire bad-fit customers.
The next version of the product was a slightly more evolved version (not much, mind you but just a very slight evolution). They leveraged existing APIs to build their v2. The contracts were stored & organized in a dropbox folder automatically for each company while e-signatures were handled via HelloSign’s API.
So they launched a free NDA creation tool on its website and quickly saw 200 companies sign up for the beta.
Users would log in, choose a contract template (NDA, sales contract, etc.), fill in key details via a web form, and Ironclad would generate a draft and send it out for e-signature – taking care of filing the completed document back in the Dropbox folder structure.
This end-to-end flow replaced what used to be many manual steps across email and different software.
Importantly, the MVP included a simple workflow checklist interface for each contract so that founders and legal teams could track the status (drafted, sent, signed, stored) at a glance. Ironclad’s early design philosophy was not to replace lawyers, but to give lawyers and businesses an “operational layer” that handles the busywork.
By focusing on common, low-risk contracts first and making the system dead-simple (no IT integration needed), the MVP quickly gained traction. The fact that Ironclad already had paying customers (for $49 or $199 monthly plans) in 2015 based on this MVP validated that users would pay for a smoother contracting workflow.
Their impressive display of agility won them a contract against 12 competing CLM providers, despite being a much smaller company. But they didn’t rest on their laurels.
They kept travelling to events in places like Boulder to observe customers using their product in real time. This revealed crucial insights about legal teams' workflows and priorities:
"They had two monitors, one showing their email and on the other was Ironclad. They were just doing their day-to-day routine, working on a legal team. And by observing them and seeing how important these routine, repeatable transactions were to their profession, we realized we had to go all in on these corporate legal teams-particularly legal operations, which was a role that was just getting defined back in 2015."
This immersive approach to customer discovery became a cornerstone of Ironclad's product development strategy. Rather than making assumptions about user needs, they watched real usage patterns and adjusted accordingly.
Thanks to Y Combinator and the founders’ networks, Ironclad’s first users were often tech startups and forward-thinking legal departments willing to try a new tool. YC’s demo day and network introduced Ironclad to companies like Gusto, HotelTonight, and others who became early customers.
Additionally, Jason’s connections in the legal community helped Ironclad land pilot trials at law firms’ corporate clients. By 2017, Ironclad had “hundreds of companies” using the platform, including notable names GoFundMe and Glassdoor.
These marquee customers served as important case studies – for example, Glassdoor’s legal team used Ironclad to manage high volumes of sales contracts and NDAs, proving the solution’s scalability beyond just tiny startups.
The free NDA tool acted as a classic lead magnet – companies would start with that single use case and then realize the value of putting more workflows into Ironclad. Meanwhile, Ironclad kept pricing attractive for growth-stage companies (low monthly subscriptions) to lower the barrier to adoption.
This bottom-up adoption model, combined with YC’s stamp of approval and word-of-mouth in the in-house legal community, propelled Ironclad’s early growth. Each successful deployment provided evidence to validate the core idea: digital contracting was indeed making legal and business teams more efficient, and there was a willingness to pay for a better way.
At the time, their competitors charged based on user seats. Ironclad turned it on its head by having unlimited users, with limited use-cases.
How Ironclad Scaled From Startup to Category Leader
When you know you’re onto something, you double down—and that’s exactly what Ironclad did.
Fresh off strong early validation, Ironclad raised an $8M Series A in 2017 led by Accel. They immediately stacked their leadership bench:
A VP of Sales, Damon Mino (bonus points: ex-lawyer and ex-DocuSign sales leader) to crack into corporate legal departments.
A seasoned COO fresh out of SalesforceIQ.
A VP of Engineering to build for the next stage of growth.
But Ironclad didn’t just throw bodies at the problem. They stayed maniacally focused on product scalability. They realized legal teams couldn't keep calling engineers every time they needed a new contract workflow.
So they launched Blueprint—a no-code workflow builder that let any legal team create, manage, and automate their own contracts.
Lawyers could finally self-serve.
Legal ops became scalable.
Ironclad had a serious moat.
Blueprint was a growth unlock. It turned Ironclad from "helpful tool" into "critical infrastructure." By the time Ironclad raised its $23M Series B from Sequoia in 2018, it was ready to go upmarket.
————————————————————————-
Moving Upmarket: From Tech Startups to Fortune 500s
With strong validation, Ironclad raised larger rounds and reinvested in scaling the team and product. The $8M Series A in 2017 led by Accel allowed Ironclad to hire talent and build out features that larger customers needed.
They hired a VP of Sales, Damon Mino (who uniquely was both a lawyer and a former DocuSign sales leader) to start targeting corporate legal departments.
They also brought in an experienced COO from SalesforceIQ and a VP of Engineering.
On the product side, Ironclad realized that to scale usage within an organization, legal teams needed to self-serve new contract workflows without relying on Ironclad’s engineers or IT. This led to developing Blueprint, released in 2018, which was essentially a no-code workflow builder for contracts.
Blueprint let customers configure their own contract templates, approvers, and business rules via a UI – a move that unlocked growth by enabling scalability. Each customer could automate many types of contracts, not just the few templates Ironclad built.
Blueprint was a key growth unlock: it was the first “walk-up usable” workflow builder for legal teams, meaning any lawyer could now encode their playbook into Ironclad without code.
This innovation both delighted customers and gave Ironclad a differentiator over competitors. By the time Ironclad closed its $23M Series B in 2018 led by Sequoia.
After establishing itself with tech-savvy mid-size companies, Ironclad began pushing into larger enterprises and diverse industries.
Ironclad’s strategy was to present itself not just as another CLM, but as a modern, end-to-end “digital contracting platform” for the whole business. This positioning helped win over Fortune 500 clients who were embarking on digital transformation in their legal and procurement departments. The $50M Series C (2019) gave Ironclad resources to expand geographically and in new verticals.
On the product front, Ironclad continued to enhance its platform’s capabilities: it launched a more advanced workflow designer in 2019 (building on Blueprint) to handle complex conditional workflows (e.g., automatically add clauses or approvers if a contract value is above X).
It also built out a robust contract repository with search and analytics, knowing that larger companies care about managing thousands of signed contracts and mining them for data
Another area of focus was integrations – Ironclad developed integrations with popular business systems (Salesforce for sales contracts, Slack and email for notifications, and cloud storage like Box/Drive for archiving) to fit seamlessly into enterprise IT ecosystems.
These enhancements made the product sticky for larger organizations. In 2020, when the COVID pandemic forced businesses to operate remotely, Ironclad’s value proposition became even clearer: fully digital contract workflows went from nice-to-have to necessity. Ironclad capitalized on this by publishing content on how companies like DoorDash used Ironclad to rapidly onboard restaurant partners or how healthcare companies shifted to telehealth contracts virtually.
Such use cases proved Ironclad could scale and handle mission-critical contracting needs under pressure. By the end of 2020, Ironclad was being recognized by industry analysts as a serious player.
Ironclad’s Series D in January 2021 ($100M) marked its arrival as a unicorn-in-waiting, with a valuation near $1 billion. This signaled confidence that Ironclad could be the category winner in digital contracting. The company used this influx to aggressively expand: it roughly doubled headcount, investing heavily in R&D (especially artificial intelligence) and customer success.
One major step was Ironclad’s acquisition of PactSafe in March 2021, bringing in a specialized team and technology for clickwrap contracts (one-click online agreements).
PactSafe’s product became Ironclad Clickwrap, allowing Ironclad clients to manage “I agree” type contracts (think of software terms of service or high-volume online sales terms) in the same platform. This expanded Ironclad’s reach from negotiated contracts into the realm of mass acceptance contracts, a strategic move to cover the full spectrum of contracting needs.
Ironclad also launched its own Ironclad Institute and Community initiatives around this time: hiring Mary Shen O’Carroll (Google’s legal operations lead) as Chief Community Officer and hosting the first State of Digital Contracting virtual conference. The message was clear – Ironclad aimed not just to sell software, but to be the hub of the legal ops community, educating the market on best practices (a move reminiscent of how Salesforce uses its community and “State of Sales” reports to drive thought leadership).
On the product side, 2021 saw Ironclad deliver on earlier promises of AI and intelligence features: it introduced functionality like AI-powered import of third-party contracts and AI contract data extraction, so businesses could ingest legacy contracts or counterparty paper and have Ironclad automatically tag key metadata.
The Series E in January 2022 ($150M at $3.2B valuation) firmly established Ironclad as a unicorn, and brought in Franklin Templeton as a new lead investor alongside all existing major investors.
Ironclad had a war chest to invest in its platform and global expansion. In 2022, the company sharpened its messaging around “Digital Contracting” as the new standard for business. CEO Jason drew an analogy: contracts needed a transformation akin to “containerization” in shipping – a standard that turns contracts into interoperable data, enabling resilience in a fast-changing world.
This narrative helped differentiate Ironclad from competitors who pitched “just CLM”; Ironclad was pitching a vision of a connected, data-rich contracting future. Practically, 2022’s big product announcement was Ironclad AI. In September 2022, Ironclad rolled out an AI layer that could “transform the way companies create, understand, and control their contracts”.
Concretely, the AI features allowed automatic extraction of key terms (like renewal dates, prices, parties) from contracts and introduced AI-driven contract review tools. Ironclad even partnered with OpenAI, integrating GPT-3 and later GPT-4 models to power some of its contract review and redlining capabilities.
This placed Ironclad at the forefront of the AI wave in legal tech, giving it a head start on an emerging growth lever.
By 2023, Ironclad’s platform had expanded to cover: contract generation and workflow (Workflow Designer), collaboration and editing (a Google Docs-like editor), e-signature (Ironclad Signature), repository and search, analytics/reporting, clickwrap, and AI assistant features – truly an end-to-end offering.
The company’s growth was also evident in customer stories: for instance, fitness company Orangetheory publicly shared how using Ironclad’s AI tools cut a typically 6-month legal project down to 3 months.
Such stories helped convince even traditional industries that Ironclad’s approach was not just hype but driving real ROI. Internally, Ironclad prepared for its next stage by realigning leadership and continuing to hire seasoned leaders in product, sales, and customer success. By late 2023, Ironclad was widely considered a leader in the contract software space, often mentioned alongside or ahead of long-time giants like Icertis.
————————————————————————-
Ironclad's Growth Levers and Strategies
Ironclad’s growth was not an accident – it was driven by deliberate strategies and levers that the company pulled at different stages to land customers like these:
Solving a Critical Pain Point Extremely Well:
From day one, Ironclad focused on making the contract process faster and easier, which delivered immediate value (time and cost savings). This clear ROI on something every business struggles with (contracts) created natural demand. As one investor noted, Ironclad was addressing “the problem of business contracting” – an unsolved problem in modern business. This strong product-market fit became a flywheel: happy legal and sales teams talked to peers about it, spreading Ironclad via word-of-mouth in the close-knit legal ops community.
Freemium and Product-Led Growth:
Ironclad smartly employed a form of freemium model in the beginning (free NDA automation) to get in the door. This product-led growth approach let potential customers test drive the value before committing. Even as it moved upmarket, Ironclad kept the product easy to try – e.g. offering demo sandboxes, on-demand videos, and a straightforward SaaS signup model (a contrast to legacy enterprise software). The ease-of-use (“walk-up usable” tools) was itself a growth lever: non-technical users could start using Ironclad with minimal training, helping it spread within organizations.
Content & Education Led Growth:
They also have a demo video library to educate users so they are taking a very education-led approach to things which helps users get in through the door, critical for product-led growth. Companies like Webflow, Typeform, Retool have all used these. You can also check out their resource libraries and stuff like that. So they are investing a lot in education to power that community.
They also have an academy which kind of ties into the whole narrative of education as well while they also show their thought leadership with the journal which is the practical angles and all things related to contract management showing a thought leadership angle. They are also ranking for key terms across contract like contract value, contract life cycle management, contract leakage and compliance and things like that. These are helping them rank on SEO for these relevant keywords and also ranking on publicity, LMS and stuff like that which is why if you are starting to create a company in this space you want to make sure that you are ranking for the correct keywords relevant to your niche and have long term keyword potential as well.
Ad Strategy:
If you look at their ad library, they also run a lot of paid ads. So you can see that they share videos on specific features or specific use cases that the corresponding feature solves. So if you look at that copy, they are always positioning Ironclad as a solution to make your contracting easier.
They are even addressing the skepticism around AI as to why different legal teams are skeptical of AI and why they should embrace AI instead. They also use keywords that are very frequent in their ICP, which is contract blockages, irritated stakeholders, because this is very true.
A lot of the contracts are siloed in one place with sales and marketing and all that stuff. And so this blockage is a problem. So they're always using the problem solution matrix to showcase their value proposition. And even their features, they run ads against like their redlining contract features. And they also share snippets on videos of customer case studies in their ads as well. So this is their entire ad strategy, which is doing tremendously well.
Community Building and Thought Leadership:
Ironclad invested heavily in building a community around legal operations and contracting. They created a content hub (“The Journal” and resource library on their site) with practical guides on contract management, published reports (like the “2021 State of Digital Contracting”), and started a popular newsletter (Pros & Contracts) for in-house legal professionals.
Hiring Mary O’Carroll, a highly respected legal ops leader, as Chief Community Officer was a strategic move to cement Ironclad’s position as a thought leader. The annual “State of Digital Contracting” event brings together customers and industry experts, generating buzz and positioning Ironclad at the center of industry dialogues. By leading conversations on how contracting is evolving, Ironclad ensures its name is synonymous with modern contracting best practices. This community focus also drives customer loyalty – users feel like they’re part of a movement, not just using a tool.
Sales Led growth:
From 2018 onward, Ironclad built a strong sales organization to complement its product-led approach. They recruited sales leaders who deeply understood the legal tech space (e.g. the VP Sales from DocuSign’s legal vertical) and scaled up a customer success team.
Ironclad identified an important fact about its user base: corporate lawyers and contract managers want a trusted relationship given the critical nature of contracts. So, Ironclad emphasized high-touch customer success, training, and support (even mentioning plans to build “the best SaaS customer support function for legal teams” after the Series B) This not only helps retain and expand accounts, but also turns customers into references for new sales.
As an example of sales strategy, Ironclad often started within a department (say sales ops managing NDAs) and then used that successful deployment to upsell company-wide CLM usage – a classic land-and-expand that its easy-to-use product facilitates.
Continual Product Innovation (Width and Depth):
A major growth strategy for Ironclad was to continuously expand its product capabilities, both in breadth (new features/modules) and depth (refinements and AI). In breadth, Ironclad went from a workflow tool to a full platform: adding the Editor (collaborative online editing), adding a Repository with advanced search, building its own e-signature (Ironclad Signature), adding Clickwrap via acquisition, and layering on AI assistants.
Each of these expansions opened up new market segments and increased the value of the platform for existing users, encouraging them to consolidate more of their contracting work in Ironclad. In depth, Ironclad consistently improved usability and performance, staying ahead of customer demands (e.g. introducing the first contextual clause library, dynamic templates, etc)
Positioning their product in the market with clear messaging:
Perhaps one of Ironclad’s most impactful growth strategies was its messaging and positioning (detailed more below).
By coining and continuously using the term digital contracting and framing their platform as the “standard for business contracting”, Ironclad set itself apart from the generic CLM (Contract Lifecycle Management) market.
This category creation approach shaped the narrative in their favor – rather than comparing feature-by-feature with competitors, Ironclad invited customers to join a larger vision of transforming how businesses handle contracts (something that sounds more innovative and strategic).
They published thought leadership pieces (like Boehmig’s 2021 blog on the need for a new contracting standard) and made “digital contracting” part of their brand. This strategy made Ironclad synonymous with the future state of the industry, which in turn attracted forward-looking customers and talent.
Messaging & Positioning in Marketing Campaigns
Ironclad’s messaging evolved as the company grew, but it always emphasized making contracting simpler and more strategic for businesses:
Early Stage Messaging: In 2015, Ironclad was described as an “automated legal assistant for companies”. Early marketing (e.g., YC Demo Day pitch, TechCrunch coverage) focused on saving startups from onerous legal paperwork and big legal bills. The value prop was very tangible: Ironclad automates drafting, organizing, and executing common legal documents so founders don’t have to pay lawyers for routine work. They often highlighted use cases like NDAs, sales agreements, and HR contracts – areas where mistakes are costly but the work is repetitive. The tone was one of empowerment: Ironclad gives startups capabilities that previously only big companies had (like a legal team), leveling the playing field.
“Contracts = Data, Not Documents” – Positioning: As Ironclad gained traction, its messaging started to hammer on the idea that contracts are more than static files – they contain data and business decisions. A line from its YC profile encapsulates this: “Contracts are business decisions trapped in administrative tasks. Ironclad is software that does all the administrative work… freeing legal teams to do more substantive work”. This messaging is powerful because it reframes Ironclad as not just efficiency software, but as a tool that unlocks the strategic value of contracts. In marketing materials and sales decks, Ironclad positioned itself as enabling legal teams to focus on high-value work (negotiating deals, ensuring compliance) while the software handles the busywork. Phrases like “single source of truth for contracts” and “operating system for your contracts” began to appear, conveying that Ironclad centralizes all contract activity and information.
Digital Contracting – Category Creation: Around 2019–2020, Ironclad’s marketing embraced the term “Digital Contracting” to distinguish its approach. Instead of calling itself just CLM software, Ironclad branding started saying “the leading digital contracting platform for modern businesses”. In press releases and the website, they would define digital contracting as “connecting the people, processes, and data involved in business contracts so companies can execute smarter agreements, faster”. The use of a new term signaled that Ironclad was something new and modern, leaving legacy competitors sounding dated. In ads and campaigns, Ironclad often educated the audience: e.g., blog posts and videos titled “What is Digital Contracting?” and why it matters. This thought leadership marketing served to both inform the market and subtly position Ironclad as the pioneer of this new category. The culmination of this was Ironclad’s bold statements in 2021 about establishing a “new standard” for business contracting – essentially claiming category leadership of digital contracting.
Emphasis on Speed, Collaboration, and Insight: Ironclad’s messaging highlights different key benefits as the product evolved. Common themes in campaigns include: Speed (“faster contracting, close deals 50% faster”), Collaboration (“connect all stakeholders in one platform, like Google Docs for contracts”), Compliance (“maintain compliance and reduce risk with standardized workflows”), and Insights (“unlock contract data for decision-making”). For instance, a 2019 Forbes piece noted Ironclad “automates and streamlines the contract process” but more importantly “also captures data from contracts” to provide business insights. This dual message – streamline process AND capture intelligence – started to appear in many of Ironclad’s marketing materials by 2019, setting it apart from tools that just stored documents. By the time of the Series E, Ironclad had focused on the “core contracting experience” and now was expanding that to a platform that connects processes across the organization, highlighting a holistic vision.
Humanizing Legal Tech: Ironclad’s tone in marketing is notably upbeat and human, which is somewhat unusual in legal tech (often perceived as dry). The company culture highlights (pictures of team events, “Community Dinners”, etc.) and values (empathy, drive, integrity) seep into the brand. In social media and blogs, Ironclad often speaks directly to in-house counsels and legal ops folks as peers, acknowledging their challenges. This was likely influenced by Jess Lee’s insight about community and caring for the user as a person. Even the naming – calling their newsletter “Pros & Contracts” (a playful twist on “pros and cons”) – shows a lighter, approachable branding. This positioning made Ironclad seem less like a stuffy enterprise software vendor and more like a modern, user-friendly brand that “gets” lawyers and business teams. That helps in an industry where change management is a hurdle; users felt Ironclad was built for them by people who understand them (indeed, Ironclad would highlight that its team includes lawyers and engineers working together).
Competitive Positioning: While Ironclad mostly focuses on positive messaging about itself, there is an implicit competitive angle: Ironclad frequently implies that alternative solutions are piecemeal or outdated. For instance, Franklin Templeton’s director in 2022 said “Other players have some components... but only Ironclad has the whole package”, calling Ironclad the “clear leader”. This quote was likely amplified in marketing to reassure buyers that Ironclad covers end-to-end needs unlike competitors. Ironclad’s content has drawn contrasts with the “status quo” of emails and Word (the manual way) and with “legacy CLMs that are clunky or narrowly focused.” By evangelizing digital contracting as a concept, Ironclad indirectly challenges competitors for not meeting that vision. In ads or collateral, you’d see phrases like “unlike old contract management systems, Ironclad is built on modern software design principles and is instantly usable” (this mirrors language from a 2022 press release). They also leaned on third-party validation in positioning – citing Gartner and Forrester rankings, Y Combinator top company lists, etc., to show that experts consider Ironclad a leader.
The Ironclad playbook:
Based on Ironclad's journey, companies looking to compete in this space-or entrepreneurs seeking to replicate their success in other markets-should consider the following playbook:
Solve a personal, painful problem: Start with a real problem you deeply understand; it ensures product-market fit is more than guesswork.
Find a cofounder with complementary skills: If you’re aiming to disrupt an industry, pair up with co-founders who cover both industry know-how and technical/build skills. It speeds up development and credibility in parallel.
Validate Early with an MVP : Identify a beachhead use case that is narrow but painful and common. Build an MVP around that, leveraging third-party services when possible to move fast. Prove that your solution works and people will use it, before expanding. Early validation (sign-ups, usage, feedback) is more convincing than any pitch deck.
Leverage Networks and Communities for Early Adoption: Plug into networks – whether an accelerator, an open-source community, or industry associations – where your early adopters congregate. Offer them something valuable (like Ironclad’s free tier) to get them on board. Their word-of-mouth and case studies will jumpstart your growth at low cost.
Land-and-Expand with a Free or Affordable Hook: Design your product and pricing with an on-ramp – a free tier or trial or entry-level package – that lowers friction to adoption. Ensure that once inside, users see the other things they could do with your product. Satisfied users will advocate internally to use the product more broadly, converting a small win into a larger deployment.
Obsess Over User Experience: If your competitors are legacy or the status quo is manual, outshine them with user experience. Even in enterprise software, end-users matter – a product that people enjoy using creates evangelists. Sweat the details to eliminate friction (Ironclad automated filing signed contracts to folders, a tiny feature that saved headaches.). A great UX in a dull space is an unfair advantage.
Build Community and Thought Leadership Around Your Mission: Become a thought leader in your domain. Share valuable insights, host events or webinars, and facilitate peer connections. If people look to your company for expertise, they will naturally look to your product for solutions. It also builds a moat – a competitor can copy features, but it’s hard to copy a loyal community.
Define (or Redefine) the Category on Your Terms: If possible, coin a term or establish a narrative that highlights your strengths and frames the market in a fresh way. Become synonymous with that vision. It’s easier to lead a new category than to fight for share in an old one. However, back it up by actually delivering on the promise of that category (Ironclad did so by continually expanding its platform and tech).
Expand Product Scope Strategically (Platform Play): Grow your product horizontally only when you have a solid base and when customers are pulling you there. Identify the next problems your users encounter once the first is solved – often those adjacent problems can be solved within your platform. By becoming a one-stop platform for related needs, you increase stickiness and value. But ensure quality in each expansion (don’t add random features that aren’t best-in-class or don’t align with your core mission).
Maintain Customer-Centricity (Success > Sales): Especially for enterprise/SAAS, invest early in customer success and support. It’s cheaper to grow an existing customer and get referrals than to constantly hunt new ones. Make your earliest customers wildly successful – their testimonials will become your strongest marketing asset. Ironclad’s early advocates (like the GC of Glassdoor) helped open doors to new clients with their success stories.