Top 10 Female Tech CEOs Transforming the IT Industry in 2026

Women‑led IT companies are building cultures that encourage diversity and accessibility. More specifically, female tech CEOs 2026 are innovating for the underserved small‑business market. They are creating platforms that streamline payroll, transform pharmacies into neighbourhood health clinics, modernise point‑of‑sale systems and make emergency response technology accessible to local governments. Their focus on practical tools and measurable outcomes aligns with the everyday needs of entrepreneurs and IT decision‑makers.

What follows is a ranking of 10 standout CEOs who are transforming the IT industry by serving the needs of small and mid‑sized businesses. The list is not limited to Silicon Valley giants; instead it highlights leaders whose solutions drive growth, efficiency and resilience for everyday entrepreneurs. 

1. Tiffany Bloomsky — Cortavo

As CEO of Cortavo, Tiffany Bloomsky has built an all‑inclusive managed IT solution tailored to small and mid‑sized businesses. Under her leadership, the company has nearly doubled its client roster in two years and expanded its service portfolio to meet demand from mid‑market organisations. Cortavo’s “More Than Managed IT” model provides fully managed services, including hardware, help‑desk support, cybersecurity, cloud services and connectivity. This approach allows small businesses to access enterprise‑level technology without the capital investment or overhead of in‑house IT.

Bloomsky’s strategy emphasises close collaboration. She recently oversaw Cortavo’s move to a state‑of‑the‑art headquarters in Atlanta with spaces designed for quarterly Executive Business Reviews and strategic planning. “This move represents more than just a new address—it’s a way to create an even better experience for our clients,” she said. The company’s new office includes a backup storage facility, underscoring its commitment to data reliability and security.

For SMB owners, Cortavo offers predictable pricing and a partnership mindset. Its service plans bundle productivity software, connectivity and cybersecurity into one subscription, freeing founders to focus on growth. Bloomsky also champions education through quarterly reviews that help clients anticipate technology needs and align IT with business goals. Cortavo’s inclusive culture, which values employee wellbeing and diversity, complements its customer‑first philosophy. (Learn more about Cortavo here and see if your organisation is a fit here.)

2. Neha Sampat — Contentstack

Neha Sampat, founder and CEO of Contentstack, leads one of the fastest‑growing composable digital experience platforms. In January 2025 the company was recognised as a “Visionary” in the Gartner® Magic Quadrant™ for Digital Experience Platforms — its first time appearing on the report. This recognition followed Contentstack’s acquisition of Lytics, a real‑time customer data platform that enriches the company’s headless CMS with gen‑AI‑powered personalization. Sampat noted that the acquisition fulfills Contentstack’s vision of delivering real‑time personalization at scale.

Contentstack’s platform allows mid‑market and enterprise organisations to publish and personalize content across multiple channels without the complexity of legacy CMS systems. The company supports the three major cloud providers (Google Cloud, Azure and AWS) and offers integrated hosting to speed deployment. Its “Care Without Compromise” program provides cross‑vendor support and resources that contribute to best‑in‑class retention. Sampat attributes the company’s success to this combination of composable technology and customer care. Iconic brands like Alaska Airlines and Burberry rely on Contentstack for digital experiences, but the platform’s modular design makes it equally valuable for mid‑market firms seeking agility.

Sampat is vocal about the need for more inclusive leadership in tech. She mentors other women founders and advocates for policies that support flexible work. Under her stewardship, Contentstack has expanded its global footprint while maintaining a culture centred on empathy and innovation. For SMBs, the ability to deliver personalized digital experiences without enterprise‑level complexity positions Contentstack as an essential tool.

3. Shrad Rao — Wagepoint

Shrad Rao co-founded Wagepoint in 2012 to simplify payroll for small businesses. The Calgary‑based company now serves more than 25,000 small businesses across North America. Although a leadership transition began in 2025, Rao’s influence as founding CEO shaped Wagepoint’s friendly, customer‑focused culture. The company’s upcoming Wagepoint 2.0 release offers faster processing, improved automation, enhanced compliance tools and a refreshed user experience. Wagepoint’s platform automates wage calculation and tax reporting, allowing owners to focus on running their companies.

Rao built Wagepoint with an emphasis on simplicity and transparency. The platform integrates with accounting software like Xero and FreshBooks and provides features such as direct deposit, automatic tax remittance and year‑end reporting. A majority investment from PSG Equity in 2020 enabled acquisitions of Timesheet Mobile and KinHR, expanding Wagepoint’s capabilities in time tracking and employee management. Despite pausing U.S. operations in 2023 to focus on its Canadian base, the company’s renewed product roadmap aims to deliver greater value for small business customers.

Rao’s leadership highlights the importance of listening to customer feedback and building products that resonate with small business owners. She emphasises that payroll should be “friendly and approachable,” aligning with Wagepoint’s brand. The company’s success demonstrates how streamlined payroll can free entrepreneurs to invest energy in growth and employee engagement.

4. Joella Almeida — MedEssist

As co-founder and CEO of MedEssist, Joella Almeida is turning community pharmacies into tech‑enabled clinics. By January 2026, the company’s Access to Care program had onboarded 100 Ontario pharmacies, equipping them to treat minor ailments and reduce pressure on emergency rooms. This milestone followed seed funding from Staircase Ventures and Hyperplane VC, which brought total investment to $6.5 million CAD.

Almeida told BetaKit that pharmacists can diagnose and treat more than 20 new conditions using MedEssist’s digital tools. The platform combines assessment workflows with digital refill, vaccine and inventory management, enabling pharmacists to issue prescriptions on the spot when no red flags are present. “If you blend pharmacies and clinics, there are way more pharmacists than physicians in Canada,” she explained. MedEssist plans to add two new treatment workflows each month and expand to more provinces and the U.S..

For independent pharmacies, MedEssist represents a new revenue stream and a way to deepen patient relationships. The company’s integration with Uber Direct (launched in 2024) enables same‑day medication delivery to more than 700 pharmacies. Almeida’s vision—using technology to empower pharmacists—addresses both healthcare accessibility and small‑business resilience. Her leadership demonstrates how women in technology can bridge healthcare and IT to serve communities.

5. Kathryn Cameron — Beauceron Security

Kathryn Cameron serves as Chief Operating Officer and Chief Revenue Officer at Beauceron Security, a cybersecurity firm focused on reducing risk for organisations of all sizes. While David Shipley remains CEO, Cameron’s leadership in operations and revenue growth has been instrumental in scaling the company’s offerings. Beauceron’s platform provides security awareness training, behavioural nudges and measurement tools that help employees understand and mitigate cyber risk. Its original Security Culture Score helps more than 1 million people assess their vulnerability to hackers.

In 2025 the company introduced the Cyber Wellness Score, a tool designed for financial institutions to help customers assess their digital vulnerability. The score functions like a fitness tracker for cybersecurity, offering personalized coaching and measuring the effectiveness of fraud‑awareness efforts. Cameron champions accessibility and inclusion in product design; she notes that building accessible software is part of Beauceron’s core values and that the company passed WCAG 2.1 Level AA certification. This commitment ensures that security tools work for diverse populations.

Cameron’s operational focus has allowed Beauceron to serve financial institutions, mid‑sized businesses and public-sector organisations. By embedding security into everyday workflows and providing actionable metrics, Beauceron helps teams change behaviour rather than simply checking compliance boxes. The company’s tools empower organisations to reduce risk before incidents occur, making cybersecurity accessible to businesses that lack internal expertise. Her leadership illustrates how operational excellence and a commitment to inclusion can drive growth in the cybersecurity sector.

6. Becca Berg — Dubsado

Becca Berg, co‑founder of Dubsado, created a business management platform to help freelancers and creative entrepreneurs automate client workflows. In October 2025 the company released Dubsado 3.0, a complete rebuild that makes the platform faster and easier to use. Over the past decade, more than 100,000 creative service businesses have trusted Dubsado to streamline invoicing, scheduling, contracts and client communication.

Dubsado 3.0 introduces a unified design system and configurable list views, allowing users to customise how they see projects, invoices and transactions. Centralized workspaces put email, invoices and forms in one location, while familiar patterns make it easier for new users to learn. Performance improvements deliver “lightning‑fast” pages and a real inbox for messages, with detachable composers, rich threading and flexible scheduled sending. An integrated time tracker, revamped calendar and node‑based workflow builder make automation more visual and intuitive.

Berg’s vision has always been to empower small businesses to focus on their craft rather than administration. The platform offers legally binding contracts, payment processing, proposal templates and client portals, making it a one‑stop solution for solo entrepreneurs. By reinvesting in the product’s design and performance, Berg ensures that Dubsado scales with its users, helping them grow revenue without sacrificing work–life balance. Her leadership underscores how women in technology leadership can create tools that are both powerful and user‑friendly.

7. Tally Mack — Bravo Store Systems

Fifth‑generation pawnbroker Tally Mack leads Bravo Store Systems, an AI‑first point‑of‑sale and enterprise resource planning platform for specialty retailers. In an interview with CIO Times, Mack explained that her company’s mission is to build a complete operating system for pawnshops, gun stores, shooting ranges and secondhand retailers. Unlike typical POS software, Bravo uses AI to give every employee “superpowers” by automating compliance monitoring, inventory categorization, pricing optimization and customer communication.

Mack notes that Bravo’s AI can analyse thousands of market data points to suggest real‑time pricing and automatically generate compliance reports, freeing staff to focus on high‑value tasks. The company serves over 2,000 customers, allowing small specialty retailers to operate at the speed and sophistication of large chains. By handling 60–70% of routine tasks through AI agents, Bravo accelerates transaction velocity and helps businesses make better buying decisions.

Mack describes her job as leading Bravo through an AI transformation and fostering an “AI‑first culture”. She focuses on hiring people who view AI as a tool to enhance human capabilities and emphasises rapid experimentation and change management. For specialty retailers, Bravo’s platform levels the playing field, allowing local shops to compete with national chains by leveraging AI‑powered insights. Mack’s story shows how women‑led companies are redefining retail technology by putting powerful tools in the hands of small‑business owners.

8. Heidi Hessler — Futurity

When tragedy struck Futurity — the original founder died in a car accident — Heidi Hessler stepped up from vice president of sales and marketing to become CEO. She guided the emergency‑management software company from a small startup to deployment in more than 32 states. Futurity’s solutions help citizens and professionals streamline emergency preparedness, response and recovery by quickly assessing damage and producing the paperwork needed to obtain FEMA funds. The platform uses mobile‑enabled tools to replace manual processes and reduce data silos.

Hessler’s leadership is characterised by resilience and a focus on community impact. Peers note that she saved the company after the founder’s death and has largely bootstrapped its growth. Futurity’s technology has been deployed in response to numerous major disaster events, providing digital tools that allow local governments and small municipalities to manage relief efforts efficiently. By digitising damage assessment and application processes, the platform shortens the time needed to secure funding, helping communities rebuild more quickly.

For SMBs and local governments, Futurity exemplifies how a women‑led IT company can deliver mission‑critical services with limited resources. Hessler continues to expand the firm’s reach while maintaining a focus on usability and accessibility. Her story underscores the importance of adaptive leadership in high‑stakes industries.

9. Seema Bansal — DCG Tech Limited

Seema Bansal, co-founder and executive director of DCG Tech Limited, has transformed the company into a leader in sustainable packaging solutions. In a 2024 interview with StartupTalky, Bansal explained that she launched DCG Tech in 2006 to provide efficient and eco‑friendly packaging to businesses seeking both cost effectiveness and environmental responsibility. Her vision is to innovate while helping clients reduce waste and enhance the consumer experience.

Since its inception, DCG Tech has achieved ISO 9001:2018 certification and built trust with more than 50,000 clients. The company opened an office in the UAE to expand internationally and established the DCG Tech Innovation Centre, a hub for research into sustainable packaging. Bansal credits the firm’s success to a combination of continuous innovation, quality management and customer‑centric solutions. Technology plays a central role: automated production lines, real‑time quality monitoring and data analytics enable DCG Tech to optimise supply chains and tailor solutions to client needs. The company also explores biodegradable and recyclable materials to reduce environmental impact.

Bansal’s story resonates with SMB owners facing sustainability mandates. Her leadership shows that responsible manufacturing and business growth can coexist. By focusing on data‑driven innovation and global expansion, she positions DCG Tech as a partner for micro, small and medium enterprises (MSMEs) seeking sustainable packaging at scale.

10. Minna Song — EliseAI

Minna Song, co‑founder and CEO of EliseAI, is applying artificial intelligence to two of life’s most complex systems: healthcare and housing. In August 2025 the company raised $250 million in Series E funding led by Andreessen Horowitz to accelerate product innovation and hire hundreds of new staff. Song said the company is built on the belief that AI can dramatically improve critical industries and noted that healthcare and housing consume about 40% of household spending. EliseAI aims to streamline these sectors with agentic AI that navigates scheduling, authorizations and customer interactions.

Since its 2024 Series D round, EliseAI has grown from 150 to over 300 employees and surpassed $100 million in annual recurring revenue. Its healthcare platform handles complex workflows from patient scheduling to prior authorizations, cutting overhead by up to 25% and reducing wait times. A testimonial from Women’s Health CT notes that EliseAI transformed call‑center operations by reducing patient wait times and improving operational efficiency. In the housing sector, the company’s AI‑Guided Tours, Lease Audits and Maintenance App help property managers tackle rising costs and labour shortages; EliseAI supports over 600 owners and operators, including 75% of the National Multifamily Housing Council’s Top 50 operators.

Song’s strategy emphasises cross‑industry impact. By integrating AI into workflows, EliseAI replaces fragmented tools with a unified platform that lowers costs and improves accessibility. The company’s rapid growth and high profile funding underscore investor confidence in its mission. For small and mid‑sized healthcare practices and property managers, EliseAI offers scalable automation that frees staff to focus on quality service rather than paperwork.

Conclusion

These ten leaders illustrate how women are redefining the technology landscape in 2026. They are not only building products; they are solving real‑world problems for small and mid‑sized organisations — automating payroll, turning pharmacies into clinics, improving cybersecurity, modernising retail operations, enabling disaster response and pioneering sustainable manufacturing. Their inspirational female tech founder stories show that empathy and innovation can coexist. Each of them has built a culture that values diversity, accessibility and customer success, demonstrating that women in technology leadership deliver results that matter.

For SMB owners and IT decision‑makers, this list serves as both recognition and a roadmap. Partnering with managed IT providers like Cortavo can accelerate growth and resilience. Investing in security awareness tools, leveraging digital content platforms and automating administrative tasks allow small teams to focus on their core mission. As you evaluate technology partners, consider reaching out to these companies — and if your business needs a comprehensive managed IT solution, contact Cortavo to explore how Tiffany Bloomsky’s team can help you thrive.