Overview

SimpleCitizen was a Salt Lake City-based legal technology startup that built a guided, software-driven platform to help immigrants navigate US citizenship and visa applications — positioning itself as "TurboTax for immigration." Founded in 2015 by Sam Stoddard, Brady Stoddard, and Aydé Soto Wright, the company raised over $6.3 million, completed Y Combinator's Summer 2016 batch, and grew to 23 employees before being acquired by Fragomen, Del Rey, Bernsen & Loewy — the world's largest immigration law firm — in September 2020. The company's core thesis was that immigration paperwork was a solvable software problem, and that a $249 flat fee could replace thousands of dollars in attorney costs. That thesis proved correct for individual consumers but hit a structural ceiling in the enterprise market: corporate buyers consistently refused to replace their immigration lawyers with software, regardless of cost savings. The resulting pivot — from consumer disruptor to law-firm infrastructure — culminated in an acquisition that validated the technology while ending the independent disruption story.

Founding Story

The origin of SimpleCitizen is unusually biographical, even by startup standards. Two of the three co-founders arrived at the same problem through independent personal experiences, giving the company a founder-market fit that was genuinely lived rather than researched.

In 2013, Sam Stoddard began the green card application process for his wife, who was originally from South Korea. When he consulted an immigration lawyer, he was told that even a straightforward case would cost thousands of dollars in legal fees. ^[3] Stoddard, who was completing a Master of Accountancy degree at Brigham Young University and had worked at KPMG and MX, recognized the inefficiency immediately: the paperwork was complex but not inherently expert-level work. ^[8]

In early 2014, Aydé Soto Wright was working in software technology in Monterrey, Mexico, when she decided to marry her Utah-native husband and move to the United States. ^[4] She navigated the same opaque, expensive system from the applicant's side — an experience that would make her not just a co-founder but the company's most credible product voice. Soto holds a bachelor's degree in Computer Science from Universidad Autónoma de Nuevo León and became SimpleCitizen's technical founder and CTO. ^[9] She would later become one of the first Mexican women to go through Y Combinator. ^[13]

The third co-founder, Brady Stoddard, brought a background in design, product, and digital marketing, and led product design at the company. ^[10]

The "TurboTax for immigration" framing emerged early. From early 2014 to early 2015, Sam Stoddard and a cousin began formally researching the market, interviewing BYU students who were struggling with green card applications. ^[5] The sample was geographically convenient — BYU's international student population provided ready access to recent immigration experiences — though it likely skewed toward a specific demographic of applicants.

SimpleCitizen was officially incorporated in February 2015, roughly a year after the research phase began, with $700,000 in seed funding and an additional $400,000 in prize and grant money. ^[23] The deliberate gap between idea and incorporation suggests the founders validated the concept before building.

The company's north star positioning — "TurboTax for immigration" — was established at launch and never changed. The analogy was precise: TurboTax succeeded by translating a complex, expert-mediated process into a guided software workflow that most users could complete without professional help. SimpleCitizen's bet was that immigration paperwork was structurally similar to tax filing: rule-based, document-heavy, and expensive primarily because of professional intermediaries rather than genuine complexity.

Timeline

• 2013 — Sam Stoddard begins green card process for his wife; told by an immigration lawyer that even a simple case would cost thousands in legal fees. Idea for SimpleCitizen is born. ^[3]

• Early 2014 — Aydé Soto Wright navigates her own US immigration process after deciding to marry her Utah-native husband and move from Monterrey, Mexico. ^[4]

• Early 2014–Early 2015 — Sam Stoddard and a cousin research the "TurboTax for immigration" market, interviewing BYU students struggling with green card applications. ^[5]

• February 2015 — SimpleCitizen officially incorporated with $700,000 in seed funding plus $400,000 in prize and grant money. ^[23]

• 2015 — Utah Governor's Office of Economic Development awards SimpleCitizen a $100,000 grant to help commercialize the product. ^[24]

• July 2015 — First version of SimpleCitizen software launches publicly. Pre-launch beta had 4,000 sign-ups but only 20 completions. Product priced at $249 with optional $99 attorney review. Available in English, Spanish, and Chinese. ^{[6] [17]}

• July 30, 2015 — TechCrunch covers SimpleCitizen's launch, establishing the "TurboTax for immigration" positioning in mainstream tech press. ^[17]

• December 2015 — First formal funding round recorded by Tracxn. ^[28]

• June 20, 2016 — SimpleCitizen announced as part of Y Combinator Summer 2016 batch — the fourth Utah startup to join YC in recent years. ^[12]

• August 22, 2016 — YC Demo Day: SimpleCitizen reports $40,000 in monthly revenue and customers in 90 countries. ^[29]

• April 18, 2017 — Fast Company profiles SimpleCitizen; company claims to have saved immigrant families "almost a million dollars" in legal fees to date. ^[31]

• November 16, 2017 — SimpleCitizen launches "SimpleCitizen for Business," an end-to-end platform for employer-sponsored work visas, targeting the $10,000–$15,000 per-hire legal fee that businesses pay. ^[20]

• September/October 2019 — Aydé Soto featured on the cover of the American Bar Association Journal's "Legal Rebels" issue. ^[42]

• November 13, 2019 — SimpleCitizen raises $5.8M Seed Plus round led by Kickstart Seed Fund, with participation from Pelion Ventures, Peterson Venture Partners, TSVC, Y Combinator, Comcast Ventures, Kima Ventures, and others. Total funding exceeds $6.3M. Round dedicated to corporate case management platform. ^[25]

• November 2019 — SimpleCitizen reports its software has saved over $16 million in legal fees to date and empowered "thousands of immigrants" to complete applications. ^[32]

• September 23, 2020 — SimpleCitizen acquired by Fragomen, Del Rey, Bernsen & Loewy — the world's largest immigration law firm — for an undisclosed amount. Becomes cornerstone of newly created Fragomen Technologies Inc. Sam Stoddard and team are retained. ^[35]

What They Built

SimpleCitizen built a guided, software-driven workflow that translated the US immigration application process into a series of plain-language questions. Users answered those questions, uploaded supporting documents, and received a completed, attorney-reviewed application package ready for submission to US Citizenship and Immigration Services (USCIS). The company described itself as "TurboTax for immigration." ^[16]

The core user experience worked in three stages. First, users answered a structured questionnaire — the software translated their responses into the correct USCIS form fields, eliminating the need to interpret government form instructions. Second, if supporting documents needed translation (a common requirement for foreign-language records), SimpleCitizen handled that step within the platform. Third, the completed application was sent to a licensed immigration attorney at the Law Offices of Jacob Sapochnick for review before submission. ^{[15] [46]}

The attorney review layer was not incidental — it was the legal architecture that allowed SimpleCitizen to operate without being classified as unauthorized practice of law. By routing completed applications through a licensed attorney, the company could offer a legally defensible service at a fraction of the cost of full legal representation.

Pricing at launch was $249 for the full application, with an optional $99 add-on for the personalized attorney review. ^[17] The company claimed this represented a 90 percent reduction in time and money compared to traditional paper applications and immigration lawyers. ^[45] The platform launched in English, Spanish, and Chinese — a deliberate choice reflecting the three largest immigrant populations in the US. ^[18]

The structural market gap that SimpleCitizen exploited was significant. USCIS had spent $3.1 billion attempting to digitize its own application process over a decade and had produced no working product. ^[44] SimpleCitizen was not waiting for the government to solve the problem — it was building the consumer-facing layer that the government had failed to create.

Product evolution followed a clear arc. The initial product covered green cards, green card renewals, and citizenship applications for individuals and families. ^[16] During the YC batch in summer 2016, the team began developing a B2B offering targeting businesses, lawyers, and HR professionals processing work visas. ^[19] Sam Stoddard acknowledged at the time that the B2B market was "a different animal compared to our successful B2C immigration products." ^[20]

In November 2017, the company formally launched "SimpleCitizen for Business" — an end-to-end platform for employer-sponsored work visas. ^[21] The value proposition for corporate customers was even more compelling than for individuals: businesses typically paid $10,000–$15,000 in legal fees for every new international hire. ^[22] The $5.8M 2019 funding round was explicitly earmarked for a corporate case management platform, signaling that SimpleCitizen had fully committed to B2B as its primary growth engine. ^[23]

What differentiated SimpleCitizen from alternatives was the combination of guided workflow, built-in document translation, and attorney review in a single flat-fee product. Competitors like LegalZoom offered document preparation but not the same end-to-end guided experience. Traditional immigration attorneys offered expertise but at a price point that excluded a large portion of the market. SimpleCitizen sat between those two options — more legally robust than a document mill, dramatically cheaper than full legal representation.

Market Position

Target Customers

SimpleCitizen initially targeted individual immigrants and their families navigating the US green card, green card renewal, and citizenship application process — a population that faced a binary choice between expensive legal representation and navigating complex government forms alone. The platform's multi-language support at launch (English, Spanish, Chinese) reflected a deliberate focus on the largest immigrant communities in the US. ^[18]

The B2B pivot, formalized in November 2017, shifted the target customer to HR departments and operations teams at companies that regularly hired international employees. ^[21] These buyers had a more quantifiable pain point — $10,000–$15,000 in legal fees per international hire — and a clear ROI calculation for adopting software. ^[22] The 2019 funding round targeted this segment further, with the corporate case management platform designed to let businesses manage their entire worker visa program through SimpleCitizen's software. ^[23]

Market Size

The US immigration legal services market is large and structurally inefficient. USCIS processes millions of applications annually across green cards, work visas, citizenship applications, and renewals. The government's own decade-long, $3.1 billion failed attempt to digitize the application process illustrated both the scale of the problem and the absence of a working solution. ^[44]

On the consumer side, the addressable market included every immigrant family navigating a green card or citizenship application without the resources to pay for full legal representation — a population that skews toward lower and middle income. On the enterprise side, the addressable market included every US employer that sponsored international hires, a segment concentrated in technology, finance, healthcare, and academia. The per-case legal fee of $10,000–$15,000 for employer-sponsored visas meant that even modest enterprise penetration could generate significant revenue per customer. ^[22]

YC Partner Dalton Caldwell articulated the market opportunity at the time of SimpleCitizen's batch: "We believe there is a huge opportunity for software to help make it easier and more affordable for people to deal with immigration." ^[16]

Competition

SimpleCitizen operated in a competitive landscape that included traditional immigration attorneys (the incumbent), document preparation services like LegalZoom (the low-cost alternative), and a growing cohort of immigration technology startups. The company's differentiation was the combination of guided workflow, document translation, and attorney review in a single product — a more complete solution than document mills and a dramatically cheaper one than full legal representation.

The enterprise segment introduced a different competitive dynamic. Large immigration law firms like Fragomen had existing relationships with corporate clients and were beginning to invest in technology to defend those relationships. Fragomen's chairman Austin T. Fragomen, Jr. explicitly framed the SimpleCitizen acquisition as a competitive response to Big 4 accounting firms — Deloitte, PwC, KPMG, and EY — which had been encroaching on immigration services for global companies. ^[40] This dynamic meant SimpleCitizen was not just competing with other startups but with the technology investment arms of the world's largest professional services firms.

Business Model

SimpleCitizen operated a flat-fee, transaction-based model on the consumer side. Users paid $249 per application, with an optional $99 add-on for personalized attorney review. ^[17] This was a one-time fee per application rather than a subscription, which meant revenue was tied directly to application volume.

The B2B product, launched in November 2017, targeted a different pricing tier. Employer-sponsored visa applications typically cost businesses $10,000–$15,000 in legal fees per hire. ^[22] SimpleCitizen's corporate platform was positioned to capture a portion of those savings, though specific B2B pricing was not disclosed publicly. The 2019 funding round was dedicated to building a corporate case management platform — a SaaS-style product that would manage ongoing visa programs for enterprise clients rather than processing individual applications. ^[23] The shift from per-transaction to recurring enterprise contracts would have significantly improved revenue predictability, though the company was acquired before that platform reached maturity.

Traction

SimpleCitizen's early demand signal was strong but revealed a significant conversion problem. During the pre-launch beta in summer 2015, over 4,000 people signed up — but only 20 completed an application through the platform. ^[30] That 0.5 percent completion rate suggested that interest in the product was high but that the application process itself — even simplified — remained a significant barrier for users.

By YC Demo Day in August 2016, roughly 14 months after launch, SimpleCitizen reported $40,000 in monthly revenue and customers in 90 countries. ^{[29] [44]} The geographic breadth was notable — 90 countries implied that the platform was being used by immigrants from a wide range of origin countries, not just the Spanish and Chinese-speaking populations targeted at launch.

The "legal fees saved" metric — a proxy for application volume — grew from "almost $1 million" in April 2017 ^[31] to "$16 million" in November 2019 ^[32] to "tens of millions" at the time of the Fragomen acquisition in September 2020. ^[33] The growth from $1M to $16M in legal fees saved over roughly 30 months represents consistent but not explosive growth — approximately 16x over 2.5 years, which is meaningful but below the trajectory that would typically support a venture-scale independent outcome.

Sam Stoddard's statement at acquisition — "We have a near perfect track record with US Citizenship and Immigration Services" ^[33] — was the company's most operationally significant claim. Application approval rates are the metric that matters most to both individual users and enterprise buyers, and a near-perfect USCIS record was a credible differentiator in a market where errors can have serious consequences for applicants.

The company grew to 23 employees by the time of acquisition. ^[34] Revenue figures beyond the $40K/month Demo Day snapshot were not disclosed publicly.

Post-Mortem

SimpleCitizen's story is not a conventional startup failure. The product worked. The team executed. The company raised institutional capital, completed YC, grew to 23 employees, and exited to a strategic acquirer. But the company did not achieve independent scale — and understanding why requires examining the specific structural ceiling it encountered in the enterprise market.

The Enterprise Veto: "We're Not Firing the Lawyers"

The pivotal moment in SimpleCitizen's trajectory was not a product failure or a funding gap — it was a sales conversation. When the company expanded into employer-sponsored visa applications and began pitching corporate customers, it encountered a consistent objection: "your technology is great, but we're not firing the lawyers." ^[37]

This was not a price objection or a product quality objection. Corporate buyers acknowledged that the software worked. They declined to adopt it as a replacement for their existing immigration attorneys. The reasons were structural: immigration status errors carry serious legal and reputational consequences for both the employee and the employer. Corporate legal and HR departments had established attorney relationships with clear liability frameworks. Replacing those relationships with software — even demonstrably effective software — introduced accountability gaps that enterprise buyers were unwilling to accept.

The attempted remedy was the B2B product itself: SimpleCitizen for Business, launched November 2017, was designed to be a complete end-to-end platform that would give companies everything they needed to manage international hiring without external attorneys. ^[21] The $5.8M 2019 round was then dedicated to building a corporate case management platform to deepen that offering. ^[23] Neither product overcame the fundamental objection: enterprise buyers wanted to augment their lawyers, not eliminate them.

The B2C Ceiling: Volume Without Velocity

The consumer product demonstrated genuine product-market fit — $40,000 in monthly revenue by August 2016, customers in 90 countries, and a legal fees saved metric that grew from $1M to $16M over 30 months. ^{[29] [31] [32]}

But the consumer immigration market has structural limitations as a venture-scale business. Immigration applications are infrequent, non-recurring events for individual users — a green card application happens once, a citizenship application happens once. The $249 price point, while dramatically cheaper than an attorney, meant that each completed application generated modest revenue. Scaling the consumer business to venture-scale returns required either very high application volume or significant price increases — neither of which was straightforward given the target demographic's price sensitivity and the infrequency of the underlying event.

The pre-launch beta's 0.5 percent completion rate (20 completions out of 4,000 sign-ups) ^[30] pointed to a persistent funnel problem: many people were interested in the product but did not complete the application. Whether this reflected the emotional weight of the immigration process, technical friction, or users ultimately choosing to hire an attorney instead was never publicly explained. The funnel problem, if unresolved, would have capped the consumer business's conversion efficiency regardless of top-of-funnel growth.

The Pivot Arrived at the Wrong Conclusion

The B2B pivot was the correct strategic response to the consumer ceiling — enterprise contracts offered higher per-customer revenue, recurring relationships, and a more defensible market position. But the pivot targeted the wrong B2B customer.

SimpleCitizen positioned itself as a replacement for corporate immigration attorneys. The enterprise market told it, repeatedly, that it would not be used as a replacement. The correct B2B customer — as the Fragomen acquisition ultimately revealed — was not corporations replacing their lawyers, but law firms augmenting their capacity. A law firm using SimpleCitizen's workflow automation could process more cases per attorney, reduce error rates, and compete on cost with Big 4 accounting firms encroaching on immigration services. ^[40]

The company recognized this reframing only after the enterprise sales process surfaced the "we're not firing the lawyers" objection. That recognition pointed directly toward Fragomen. Sam Stoddard framed the acquisition as the logical conclusion: "Culminating our years of work by partnering with the largest immigration law firm in the world just puts us into the perfect position to have as much impact as possible." ^[38]

The Competitive Pressure That Accelerated the Exit

Fragomen's acquisition rationale was explicitly competitive. The firm's chairman stated that the acquisition was intended to help Fragomen compete with Big 4 accounting firms — Deloitte, PwC, KPMG, and EY — which had been expanding into immigration services for global companies. ^[40] This meant SimpleCitizen was acquired not because it had built a dominant consumer business, but because it had built the best available immigration workflow technology at a moment when the world's largest immigration law firm urgently needed it.

The timing — September 2020, nine months into a global pandemic that had dramatically disrupted international travel and immigration — may have also influenced the acquisition. COVID-19 created both urgency (law firms needed technology to serve clients remotely) and uncertainty (immigration volumes were suppressed), potentially making an acquisition more attractive to both parties than continued independent operation.

The Funding Gap Between Ambition and Scale

SimpleCitizen raised approximately $6.3–$7.85M in total funding across its lifetime (sources conflict on the precise figure). ^[26] The $5.8M 2019 round was the company's largest single raise and was dedicated to building the corporate case management platform. ^[25] The acquisition came less than 11 months after that round closed.

The rapid sequence — large seed round in November 2019, acquisition in September 2020 — suggests either that the corporate platform development revealed the enterprise adoption ceiling more clearly than expected, or that the acquisition opportunity was compelling enough to pursue before the platform reached maturity. The undisclosed acquisition price makes it impossible to assess whether investors received a strong return on the ~$7M deployed, though the retention of the founding team and the creation of a dedicated Fragomen Technologies subsidiary suggests the deal was structured to reward the team's continued contribution. ^[36]

Key Lessons

• The "TurboTax for X" model breaks down when enterprise buyers face liability exposure. TurboTax succeeded because individual tax filers bear their own liability for errors. In enterprise immigration, the employer bears legal and reputational risk for visa errors affecting employees. That liability asymmetry makes corporate buyers unwilling to replace attorneys with software, regardless of cost savings — a structural constraint that no amount of product improvement can overcome. SimpleCitizen's enterprise sales process surfaced this objection consistently, and the company's response (building a better B2B product) addressed the wrong variable.

• The correct B2B customer in regulated professional services is often the professional, not the professional's client. SimpleCitizen spent years trying to sell to corporations as a replacement for immigration attorneys. The acquisition by Fragomen revealed that the natural buyer was the law firm itself — a customer that could use the technology to increase capacity and reduce costs without eliminating the attorney relationship that enterprise clients required. Identifying the law firm as the primary B2B customer earlier might have changed the company's go-to-market strategy and potentially its growth trajectory.

• A near-perfect regulatory track record is a durable competitive asset in legal tech. Sam Stoddard's claim of a "near perfect track record with USCIS" ^[33] was not marketing language — it was the company's most defensible product claim and likely its most important acquisition asset. In markets where errors carry serious consequences for end users, demonstrated accuracy is more valuable than feature breadth or price. Legal tech companies that can quantify their approval or accuracy rates relative to human professionals have a credible enterprise sales argument that pure workflow tools lack.

• Founder-market fit grounded in personal experience provides authentic positioning but may narrow the initial research sample. SimpleCitizen's founding story — two co-founders who personally navigated US immigration — gave the company genuine credibility and a clear product intuition. But the initial market research was conducted primarily through BYU students, a sample that likely skewed toward international students and LDS missionaries' foreign spouses. ^[5] Broader early research might have surfaced the enterprise adoption ceiling sooner and accelerated the pivot toward law firms as the primary B2B customer.

• Acquisition by the market incumbent is a legitimate outcome for legal tech companies that build real workflow automation. SimpleCitizen's exit to Fragomen was not a distressed sale — it was a strategic acquisition by a firm that needed the technology to compete. The founding team was retained, the technology became the cornerstone of a new subsidiary, and the company's mission (making immigration more accessible) continued under new ownership. For companies building in regulated professional services, where independent disruption faces structural limits, positioning as infrastructure for the incumbent can be a more achievable and durable outcome than displacing the incumbent entirely.

Sources

1. SimpleCitizen About Page — Founding Story
2. SimpleCitizen Newsroom — Founder Bios
3. Fast Company: "The Business That Love Built" (April 18, 2017)
4. Yahoo Finance / PR: SimpleCitizen Accepted to Y Combinator Summer 2016 (June 20, 2016)
5. TechCrunch: "SimpleCitizen Makes Obtaining A Green Card More Manageable" (July 30, 2015)
6. Y Combinator Blog: "SimpleCitizen is TurboTax for Immigration"
7. GlobeNewswire: SimpleCitizen Launches End-to-End Business Visa Platform (November 16, 2017)
8. GlobeNewswire: SimpleCitizen Announces $5.8M Seed Plus Funding (November 13, 2019)
9. PR Newswire: Fragomen Acquires SimpleCitizen (September 23, 2020)
10. TechBuzz News: SimpleCitizen Acquired by World's Largest Immigration Law Firm
11. TechCrunch: Y Combinator Demo Day Summer 2016 (August 22, 2016)
12. ABA Journal: Legal Rebels — SimpleCitizen Feature
13. FinSMEs: SimpleCitizen Raises $5.8M (November 14, 2019)
14. Tracxn: SimpleCitizen Company Profile
15. Y Combinator: SimpleCitizen Company Page
16. Laborless Blog: Immigration Tech in 2020 — Acquisitions, Partnerships, VC Funding (January 9, 2021)
17. Pulse2: SimpleCitizen $5.8 Million Funding (November 19, 2019)
18. Product Hunt: SimpleCitizen Launch Page
19. Wayback Machine: SimpleCitizen.com Archive circa 2016
20. Hacker News: SimpleCitizen (YC S16) Is TurboTax for Immigration
21. Hacker News: Startups that launched at Y Combinator S16 Demo Day 1