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Stiira

Stiira is a specialized SaaS solution designed to help companies effectively manage the complexities of government-regulated leaves of absence (FMLA, ADA, Paid Family Leave).

Portland, OR, USA

One Liner

One Liner
Stiira is a specialized SaaS solution designed to help companies effectively manage the complexities of government-regulated leaves of absence (FMLA, ADA, Paid Family Leave).

What Problem We are Solving

Problem
Stiira's integration-friendly software is designed to address the lack of functionality in many HCM platforms when it comes to tracking compliance-heavy leaves of absence like Paid Family Leave, FMLA, ADA.

About Us

About Us
Stiira is a Portland, Oregon-based software company that specializes in providing innovative leave management solutions for employers managing leave in-house and third-party administrators offering leave services. With over 30 years of collective HR experience, the Stiira team is comprised of passionate innovators dedicated to driving the next generation of leave management technology. Stiira's name is taken from the Swedish word styrskena, which means “guideway,” aligning with the design and functionality of our software, which helps organizations navigate the complexities of managing government-regulated leaves of absence. Recognizing the significant gap in the market for robust yet affordable leave software, our mission is to equip all employers with a powerful solution that simplifies this complicated landscape, regardless of size, location, and budget. 

Venture Highlights

Highlights
Since launching in February 2023, Stiira has achieved significant milestones that demonstrate strong product-market fit, growing investor interest, and effective growth strategies to accelerate traction.

Stiira currently serves sixteen customers, generating $347K in revenue to date, with $218K in annual recurring revenue (ARR). Driven by a well-optimized marketing engine, third-party channels, and strategic partnerships, Stiira’s pipeline continues to expand, with 36 pending deals representing a potential $831K in ARR. Our customer base reflects key target market segments, including five employers managing leave in-house and two third-party administrator (TPA) customers offering outsourced leave management services to a growing client base. Through TPA partnerships, Stiira now supports leave management programs for over 120 companies and 13,000 active users.

Significant progress has been made toward establishing Stiira as the most integrated leave management platform within major human capital management (HCM) systems. We currently offer live integrations with Dayforce and Paycom, with UKG and ADP integrations underway. Market research and customer feedback consistently highlight the need for specialized leave management solutions to bridge compliance gaps and meet tracking requirements, even among organizations with existing HCM systems. Our integration-driven growth strategy has resulted in a 20% increase in add-on revenue from existing customers, alongside successful upselling of new capabilities to secure warm deals.

On the funding front, Stiira excelled in the 2024 & 2025 pitch competition circuit, securing first place at Westside Pitch 2024, Pitch Willamette 2024, Pegasus Lightning Round III and OEN AOTech 2025. Combined with additional angel investments, these successes have contributed to a total of $753K raised to fuel our growth.

Additional highlights include a strategic marketplace partnership with isolved, an HR technology partnership with VirgilHR, and Stiira’s recent recognition on HR Technology Advice’s 2025 Cool HR Tech List.

Business Model

Business Model
  • SaaS B2B subscription-based pricing model with tiered plans for employers and TPAs of different sizes. 
  • Additional revenue from value-added services such as integrations, custom system setup, consulting, and rev share agreements with partners.

Competitive Advantage

Quote

Competitive Advantage


Stiira is built by leave experts to be an affordable, yet robust option for employers and TPAs. Due to advances in technology over the past 10 years, Stiira offers a much more affordable and flexible product than what the current industry leaders have. Our software solution is powerful, sleek, and integration friendly; and comes at a fraction of the price of our competitors. It is also highly customizable and the power to make changes is given directly to the administrator. This significantly reduces the time and effort typically associated with implementation and support requests.

Unique Differentiators:

  • TPA Specialization: Stiira was incubated within an HR outsourcing company, making it the only leave management solution designed specifically for the third-party administrator (TPA) model. Our architecture, pricing structure, and partnership approach are tailored to meet the unique needs of TPAs launching and scaling leave services. This specialization creates a strong competitive moat, enabling Stiira to adapt seamlessly to market fluctuations between insourcing and outsourcing.

  • Adaptable Compliance: Navigating the complex and ever-changing landscape of leave regulations is one of our core strengths. Unlike legacy systems that rely on slow backend updates, Stiira brings compliance configuration to the frontend. Our dynamic templates cover federal and state-specific regulations and allow administrators to quickly adapt to new requirements. Built-in tools like action lists, required notices, and automated email notifications streamline compliance management with minimal lag.

  • Integration-Focused: Stiira is engineered for seamless compatibility with all major Human Capital Management (HCM) systems to complete the HR technology stack. We prioritize real-time API integrations over outdated file-feed imports, enabling automated workflows and real-time data synchronization. Our flexibility in custom integrations helps us explore new verticals with clients and increases customer retention by aligning with the HR platforms they already use.

  • Flexible Configuration: Our multi-tenancy architecture gives administrators complete control to customize policies, roles, and system settings based on service providers, employers, subgroups (e.g., entities, unions, departments), and self-service options. This flexibility is a significant advantage for both TPAs and employers managing leave in-house, especially those with complex organizational needs.

  • User Experience: Stiira is designed with simplicity and modernity in mind. Administrators and employees consistently praise our clean user interface and intuitive role-based functionality as a refreshing alternative to legacy HR software. This focus on usability reduces the learning curve, enhances efficiency across teams, and removes barriers to stakeholder buy-in, which is typically a pain point for HR teams implementing new systems.

  • Customer-First Approach: Our competitive pricing, guaranteed support response times, and rapid implementation process are designed to exceed customer expectations. Market research shows that customers often seek an alternative to competitors due to dissatisfaction with support, pricing, or implementation delays. Stiira’s commitment to exceptional customer experience, from the first sales call to ongoing support, sets us apart in the market.

Revenue

Revenue To Date
$348K
MRR
$18.2K
Revenue YTD
$245K
Burn Rate
$18.5K

Users

Total Users
13K
Total Users (Past 30 Days)
8.28K
Daily Active Users
25
Monthly Active Users
244
Total Paying Users
8.28K
MoM Growth Users
11%
Organic Traffic %
50%

Customer Costs

CAC
$29K
LTV
$91.2K
Churn
17%
Margins
98%

Go-To Market Strategy

Business Strategy

Inbound Marketing Engine

Web Optimization
Search Engine Optimization (SEO) efforts and content creation to increase traffic to our website. Key elements of optimization efforts include:
  • Ongoing analysis for improved SEO results
  • Scheduled blog posts and downloadable assets
  • Call-to-actions
  • Scheduled social media posts 

Email Campaigns
Ongoing communication with contact list to increase top of funnel engagement. Key activities include:
  • Monthly newsletter to full contact list
  • Monthly promotional campaigns to contact list segments by location, employer type, and industry
  • Email campaigns tied to asset downloads and form fills

HCM Integration Marketplaces 

Prioritization placed on HRIS, Payroll, and Benefits technology marketplace partnerships to tap into additional vendor communities to expand our marketing reach and customer-base. This involves integrating with adjacent HR software solutions to complete their “tech stack” and gain access to their existing customer base. Current target partners include:

  • isolved (launched in April 2024)
  • Dayforce (integration live!)
  • Paycom (integration live!)
  • Paychex (approved partner – weighing cost)
  • NEO GOV
  • ADP (building integration in Q1 2025)
  • Paylocity (Integration built)
  • Workday
  • PrismHR (NDA signed – in discussions)
  • Rippling
  • HiBob (approved partner – weighing cost)
  • UKG (currently building out integration)

Strategic Partnerships

Trüpp Partnership
Leverage partnership with Trüpp to reach an established network that encompasses our target market. By collaborating with Trüpp, Stiira was able to increase reach immediately after product launch, giving a boost to contacts and leads for future marketing opportunities. Co-marketing activities include email campaigns, co-hosted webinars, and referral process between sales teams.

VirgilHR Partnership
Formed a referral partnership with VirgilHR, an HR compliance platform designed to help SMB’s navigate the complexities of employment and labor law. This partnership will help provide additional marketing, sales, and revenue opportunities (rev share agreement in place).     

HR Answers Partnership
Recently launched a strategic referral partnership with HR Answers, a respected HR consulting and outsourcing firm that has supported over 10,000 organizations, particularly in the public sector across Oregon and Washington. This collaboration opens new channels for marketing, sales, and revenue growth through warm referrals and increased visibility in a key regional market. Our first referral from HR Answers is already progressing well and shows strong potential to convert into a new customer.

Professional Network
Arranged Stiira introduction and demo sessions with Trüpp’s partners to establish an initial client base and network of potential resellers.

Benefit Broker Roadshow
Series of product demos aimed to introduce Stiira to brokers to inform extended network of solution available to employers. Introductory demos completed with the following benefit brokers:

  • IMA
  • Spring Consulting Group
  • Brown & Brown
  • OneDigital
  • USI
  • HUB
  • Marsh & McLennan
  • CU Benefits Alliance
  • McGohan Brabender
  • Alliant
  • The Horton Group
  • PayneWest Insurance
  • Gallagher
  • Epic Insurance
  • Woodruff Sawyer
  • Lockton
  • CBIZ

Multi-Channel Placements

Vendor Directories & Associations
Paid directory placements and social profiles to extend reach to HR consulting networks. Set up and optimized profiles for the following vendor directories/associations:

  • BenefitPitch
  • Shortlister
  • SHRM (paid advertising placement in addition to directory)
  • G2
  • Capterra
  • GetApp
  • Software Advice
  • USI
  • DMEC
  • PartnerStack
  • SaaSHub
  • Dimmo

Sales Strategy 


Inbound Prospecting 
Stiira utilizes an inbound sales strategy to attract potential customers to our business through marketing efforts, blog content, and webinars, providing our prospects with valuable industry information and introducing the solution that address their pain points. A high-level overview of the process is outlined below:

1.     Attract: Instead of simply identifying potential buyers, we focus on attracting them through valuable content and targeted outreach. We begin by defining and refining Stiira's Ideal Customer Profile (ICP) through market research, social listening (primarily LinkedIn), and analysis of existing customer data. This process allows us to pinpoint prospects most likely to benefit from our solution. We prioritize inbound leads who actively engage with our content (e.g., download resources, attend webinars, fill out forms) as they demonstrate a higher level of interest. We also use targeted LinkedIn campaigns to reach specific segments of our ICP.
2.     Engage: This stage emphasizes meaningful engagement. We initiate personalized outreach through various channels (email, LinkedIn, phone) based on the prospect's preferred communication method and their specific needs. Our messaging is tailored to their industry, role, and pain points, referencing content they've interacted with. We focus on building relationships and understanding their challenges through consultative conversations. We utilize pre-designed conversation guides and discovery call frameworks to ensure consistency and effectiveness in our exploratory conversations. We also offer valuable resources (e.g., checklists, templates, ROI calculators) relevant to their needs.
3.     Convert: At this stage, the focus is on converting qualified leads into customers. Our sales team acts as trusted advisors, providing personalized recommendations and demonstrating how Stiira solves the prospect's specific challenges and pain points. We go beyond general information by uncovering the buyer's context and tailoring our proposition accordingly. We leverage case studies, testimonials, and product demos to showcase the value of Stiira and address any remaining objections. We strive to create a seamless and transparent closing process.
4.     Onboard: This new stage emphasizes post-sale customer success. We focus on smooth onboarding, ongoing support, and building long-term relationships. We actively seek feedback and encourage satisfied customers to become advocates for Stiira through testimonials, referrals, and reviews. The onboarding process helps fuel further inbound growth.

Outbound Prospecting
Our overall sales strategy is primarily driven by an inbound marketing & sales approach (see above), where the sales team will follow up with and pursue warm leads who are attracted to Stiira by content-driven marketing tactics. However, we take the approach of complementing the flow of inbound leads with an outbound sales push for the following reasons:   

·        Powerful complement to inbound marketing: Outbound prospecting can be used in conjunction with inbound marketing to provide a more comprehensive marketing strategy.
·        Personalization: Outbound prospecting can be personalized to target specific individuals, businesses, or industry segments most likely to be interested in our products or services.
·        Tracked and measurable: Outbound prospecting can be tracked and measured to determine its effectiveness and identify areas for improvement.

Lead Generation 
To complement the flow of inbound leads generated from our marketing activity, we use a data mining tool called Seamless AI. This platform allows the sales team to data mine target prospects and contact information (phone number, email, and address). We use this information for cold outreach via email campaigns, phone calls, newsletters, and webinar invitations.   

Competitive Analysis

Competitive Analysys
There is a significant gap in affordable, yet robust, options for non-enterprise employers and few solutions out there truly built specifically for third-party administrators (TPAs) offering leave services. In the current market most software solutions fall into a certain category. Industry mainstays like AbsenceSoft and Qcera are often seen as too expensive and overly sophisticated for our mid-market target customer group.  Others are not specialized or sophisticated enough.  Leave solutions from companies like Paylocity, ADP, or UKG come in the form of clunky add-on modules for their HRIS or payroll platform.  These options act much like time and attendance tools, often missing the mark on more intricate leaves pertaining to state, local, or company guidelines.  Another category sees players like JJ Keller simply offering glorified spreadsheets.
Competitor Website
J.J. Keller FMLA Manager www.jjkeller.com
Qcera qcera.com
AbsenceSoft absencesoft.com

Networking

Networking
We are open to meeting up to grab a coffee, or just to chat. We would really enjoy your feedback and insight into our venture and would be happy to discuss anything that you are currently working on to see if we can be of service!

DEI

Number of Founders
4
Gender
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First-Generation College Student(s)
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Veterans
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Ethnicity
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Share

Capital

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Name Amount
Amount Left $247,000.00
Amount Raised (This Round) $753,000.00
Amount Raise To Date $753K
Investment Type Post-money
Type of Raise SAFE

Valuation
$7M
Friends & Family
$490K
Preseed
$68K
Seed Bridge
$195K

TAM SAM SOM

TAM
$10.6B
SAM
$2.65B
SOM
$265M

Business Stage

Business Stage
Paying Customers

Business Type

Business Types
Investor-Backed

Categories

SaaS
B2B
Technology

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Last Updated: 01/18/24