# Andrea Kowalski

> Andrea Kowalski is a Series A investor at Bailador Technology Investments backing Software. See 5 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [Bailador Technology Investments](https://shizune.co/investors/profile/bailador)
- Location: New York, United States
- Total investments: 5
- Last investment: Jan 2022
- Lead investor: 100%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/akowalski/
- X (Twitter): https://twitter.com/dre_kowalski
- Website: https://www.tidalvc.com

Andrea Kowalski is a Series A investor at Bailador Technology Investments in New York focused on Software and SaaS. Andrea Kowalski

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 2 | 40% |
| SaaS | 1 | 20% |
| EdTech | 1 | 20% |
| Retail | 1 | 20% |
| Big Data | 1 | 20% |

16 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Series A | 2 | 40% |
| Seed | 1 | 20% |
| Series B | 1 | 20% |
| Funding Round | 1 | 20% |

### Country

| Country | Investments | Share |
| --- | --- | --- |
| Australia | 2 | 40% |
| United States | 1 | 20% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Checkbox | Checkbox provides an AI-powered no-code workflow automation platform that helps legal operations and in-house legal teams capture, manage, and automate work requests and processes from multiple communication channels such as email, Slack, Teams, and CRM systems. The company’s software centralizes intake, triage, matter tracking, and reporting intoa unified service hub that reduces manual administrative effort and improves visibility across legal workstreams. Its platform includes features for workflow design using visual drag-and-drop tools, AI-driven request categorization, matter management, document generation, and analytics to support operational oversight and decision-making. Checkbox also offers customizable self-service tools and an AI chatbot assistant that interacts with users in natural language to route tasks, generate outputs, and link to automated processes. The company’s solutions are designed to integrate with existing systems via APIs and support automation of approvals, compliance checks, and routine tasks without requiring coding expertise. Businesses use the platform to streamline legal workflows, improve service delivery, and gain structured insights into workload and performance across enterprise functions. | $4.4M | Seed | Jan 27, 2022 |  |
| Checkbox | Checkbox provides an AI-powered no-code workflow automation platform that helps legal operations and in-house legal teams capture, manage, and automate work requests and processes from multiple communication channels such as email, Slack, Teams, and CRM systems. The company’s software centralizes intake, triage, matter tracking, and reporting intoa unified service hub that reduces manual administrative effort and improves visibility across legal workstreams. Its platform includes features for workflow design using visual drag-and-drop tools, AI-driven request categorization, matter management, document generation, and analytics to support operational oversight and decision-making. Checkbox also offers customizable self-service tools and an AI chatbot assistant that interacts with users in natural language to route tasks, generate outputs, and link to automated processes. The company’s solutions are designed to integrate with existing systems via APIs and support automation of approvals, compliance checks, and routine tasks without requiring coding expertise. Businesses use the platform to streamline legal workflows, improve service delivery, and gain structured insights into workload and performance across enterprise functions. | $4.2M | Series A | Jan 27, 2022 |  |
| BROSA | We started Brosa because we found it so painful (countless weekends wasted, uninspiring products, no assistance from staff, no updates post-purchase, deliveries not showing up) to buy furniture ourselves from traditional retailers. We asked ourselves, "how do we use technology to make this experience simpler?" Fast forward 7 years,we've built tech (and the operations) to continuously solve for this.> QR-codes on every piece of furniture to track who made it, who moved it & when it all happened (to reduce lost inventory and improve quality control). > Live inventory progress tracing and ability for a customer to buy a specific piece of inventory whilst it's still being made on the other side of the world. > Omnichannel tech to enable offline shopping experiences to seamlessly continue online (go into a store, talk to our staff and then go home and buy the items you discussed, on your own device). > When we started our own delivery fleet (yes, we did that also) - we automated the delivery scheduling (human-like conversational text messaging to schedule in a suitable delivery date). | $3.4M | Series A | Oct 24, 2017 |  |
| BROSA | We started Brosa because we found it so painful (countless weekends wasted, uninspiring products, no assistance from staff, no updates post-purchase, deliveries not showing up) to buy furniture ourselves from traditional retailers. We asked ourselves, "how do we use technology to make this experience simpler?" Fast forward 7 years,we've built tech (and the operations) to continuously solve for this.> QR-codes on every piece of furniture to track who made it, who moved it & when it all happened (to reduce lost inventory and improve quality control). > Live inventory progress tracing and ability for a customer to buy a specific piece of inventory whilst it's still being made on the other side of the world. > Omnichannel tech to enable offline shopping experiences to seamlessly continue online (go into a store, talk to our staff and then go home and buy the items you discussed, on your own device). > When we started our own delivery fleet (yes, we did that also) - we automated the delivery scheduling (human-like conversational text messaging to schedule in a suitable delivery date). | $3.4M | Series B | Oct 24, 2017 |  |
| Instaclustr | Instaclustr delivers reliability at scale through an integrated data platform of open source technologies such as Apache Cassandra®, Apache Kafka®, Apache SparkTM, RedisTM and ElasticsearchTM. Instaclustr allows companies to focus internal development and operational resources on building cutting edge customer-facing applications. Instaclustr nowhas more than 100 million node hours and 7 PB of data under management across its open source technology suite | $4.7M |  | Nov 23, 2016 |  |

5 of 5 investments shown.

## Co-investors
- [Airtree Ventures](https://shizune.co/investors/profile/airtree-ventures-2) — VC Fund, 2 deals together
- [ANU Connect Ventures](https://shizune.co/investors/profile/anu-connect-ventures) — VC Fund, 1 deal together
- [OIF Ventures](https://shizune.co/investors/profile/our-innovation-fund) — VC Fund, 1 deal together
- [Surge](https://shizune.co/investors/profile/surge-ahead) — VC Fund, 1 deal together

## About Bailador Technology Investments

VC Fund · Sydney, Australia

Bailador is a growth capital fund that focuses on the IT and media sectors, managed by an experienced team with demonstrated sector expertise. The company supports its portfolio companies in subsequent rounds of funding through their own participation and with introductions to larger international growth expansion funds. It assists in thepreparation and management of fundraising, M&A activity, and pre-IPO processes. The portfolio businesses of the company are DocsCorp, Click Loans Group, Rezdy, Stackla, iPRO Solutions, and SiteMinder.Bailador is an Australia-based company that was founded in 2010 by Paul Wilson and David Kirk.

4 contacts available at Bailador Technology Investments.

| Name | Title | Profile |
| --- | --- | --- |
| David Kirk | Co-Founder, Partner | https://shizune.co/investors/profile/david-kirk-2 |
| James Johnstone | Investment Director | https://shizune.co/investors/profile/james-johnstone |
| Paul Wilson | Co-Founder, Partner | https://shizune.co/investors/profile/paul-wilson-7 |
| Andrea Kowalski | Partner | https://shizune.co/investors/profile/andrea-kowalski |

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## FAQ

### What does Andrea Kowalski invest in?

Andrea Kowalski invests primarily in Software, SaaS and EdTech startups, most often at Series A and Seed stage. Most of the 5 investments tracked by Shizune back companies in Australia. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### When did Andrea Kowalski last invest?

The most recent investment recorded for Andrea Kowalski closed in Jan 2022. Shizune tracks 5 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.

### Is Shizune's investor data accurate?

Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.

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