# Andrew Cleland

> Andrew Cleland is a Series A investor at Techstars backing Software and Machine Learning. See 17 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [Techstars](https://shizune.co/investors/profile/techstars)
- Location: New York, United States
- Total investments: 17
- Last investment: Jan 2025
- Lead investor: 41%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/acleland/
- X (Twitter): https://twitter.com/awcleland
- Website: https://x.com/awcleland
- Facebook: https://www.facebook.com/awcleland

Andrew Cleland is a Series A investor at Techstars in New York focused on Software and Machine Learning. Andrew Cleland is the current Chief Investment Officer of Techstars. He previously worked at CopyCat as a Board Member. Andrew Cleland attended INSEAD.

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 4 | 24% |
| Machine Learning | 3 | 18% |
| Information Technology | 3 | 18% |
| Artificial Intelligence | 3 | 18% |
| E-Commerce | 2 | 12% |

39 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Series A | 3 | 18% |
| Series C | 3 | 18% |
| Seed | 2 | 12% |
| Series B | 2 | 12% |
| Series D | 2 | 12% |

7 stages tracked in total.

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| First Ascent Biomedical | AI-designed personalized combination cancer therapy plans, built for individual cancer patients from the bottom up | $6M | Seed | Jan 13, 2025 |  |
| First Ascent Biomedical | AI-designed personalized combination cancer therapy plans, built for individual cancer patients from the bottom up | $6M |  | Jan 13, 2025 |  |
| EvaBot | Eva is the easiest way to send personalized corporate gifts at scale. Never worry about preferences or delivery details again. Just cc Eva in an email or chat on Slack.Eva's machine intelligence matches hip product companies with the unique interests and attributes of the gift recipient. The result is a perfect automated gift from acurated list of vendors. | $8.3M | Series A | Jul 28, 2022 |  |
| Enigma Technologies | Enigma Technologies, a New York-based data science company, is building the future of small business intelligence. Enigma provides timely, accurate insights on the identity, activity, and risk profile of every small business. From evaluating insurance risk to fraud prevention, Enigma helps businesses better serve their SMB customers. Leadingorganizations, including American Express, Truist, and PayPal depend on Enigma to power the daily decisions that matter. | $95M | Series C | Sep 18, 2018 |  |
| SundaySky | SundaySky combines the power of personalization with the emotion of video to transform customer relationships, one person at a time. Its proprietary SmartVideo™ Marketing Cloud powers billions of personalized video experiences annually for the world's leading brands, including AT&T, Allstate, Citigroup, Saks Fifth Avenue, Staples, Verizon,and more. In 2017, SmartVideo generated more than $1.4 billion in measured value for SundaySky customers. Headquartered in New York City, SundaySky has additional offices in Tel Aviv and Tokyo. | $7M | Series D | Aug 01, 2017 |  |
| Interactions | Interactions develops and markets award-winning natural language understanding technology used by Fortune 500 companies worldwide. Built on its patented Adaptive-Understanding™ technology that seamlessly integrates both human and machine intelligence, Interactions provides highly conversational virtual assistant solutions. Companies such as Hyatt,Best Western, Humana, TXU Energy, Asurion and AllConnect deploy Interactions’ solutions,The company’s sales, service and support solutions are delivered across any device with type, touch or talk capabilities, and have handled more than one billion transactions to date. Rooted in natural speech recognition and built to adapt to human conversation, Interactions’ solutions have delivered cost-savings and increased efficiencies in sales and support for some of the largest companies in the world. Interactions Corporation, founded in 2004, is headquartered in Franklin, Massachusetts and has additional offices located in Bedminster, New Jersey, New York, New York, Indianapolis, Indiana and Austin, Texas. | $56M |  | Aug 09, 2016 |  |
| SundaySky | SundaySky combines the power of personalization with the emotion of video to transform customer relationships, one person at a time. Its proprietary SmartVideo™ Marketing Cloud powers billions of personalized video experiences annually for the world's leading brands, including AT&T, Allstate, Citigroup, Saks Fifth Avenue, Staples, Verizon,and more. In 2017, SmartVideo generated more than $1.4 billion in measured value for SundaySky customers. Headquartered in New York City, SundaySky has additional offices in Tel Aviv and Tokyo. | $30M | Series D | Jun 08, 2016 |  |
| Windsor Circle | Windsor Circle provides eCommerce, retail, and customer intelligence software to online marketers to automatically build and update customer segments based on purchase history information. The company offers an all-in-one Retention Marketing Platform that integrates clients’ eCommerce and email platforms; provides automated analysis of theircustomer, product, and purchase data; and enables instant marketing action by updating targeted customer segments in their email accounts. It allows clients to integrate their eCommerce, analytics, and email platforms; helps retailers to connect, analyze, and act; and provides retention marketing strategy and automation solutions. The company provides retail, customer, and business intelligence solutions. Windsor Circle was incorporated in 2011 and is based in Durham, North Carolina. | $4.1M | Series B | Apr 28, 2016 |  |
| FanDuel | FanDuel, launched in July 2009, is the undisputed leader in the one-week fantasy sports industry. Offering fantasy sports for NFL, MLB, NBA and NHL FanDuel targets the 30+ million adult fantasy sports players in North America. Players draft fantasy sports teams at any time of the season in head-to-head or multi-player contests, paying an entryfee for each contest and vie for cash prizes. In 2013 the company awarded over $150m in prizes and is on course to award over $400m in 2014.The company currently has over 100 employees and is headquartered in New York. | $275M | Series E | Jul 14, 2015 |  |
| Enigma Technologies | Enigma Technologies, a New York-based data science company, is building the future of small business intelligence. Enigma provides timely, accurate insights on the identity, activity, and risk profile of every small business. From evaluating insurance risk to fraud prevention, Enigma helps businesses better serve their SMB customers. Leadingorganizations, including American Express, Truist, and PayPal depend on Enigma to power the daily decisions that matter. | $28.2M | Series B | Mar 22, 2015 |  |

10 of 17 investments shown.

## Co-investors
- [Amex Ventures](https://shizune.co/investors/profile/american-express-ventures) — VC Fund, 3 deals together
- [Bullpen Capital](https://shizune.co/investors/profile/bullpen-capital) — VC Fund, 3 deals together
- [Globespan Capital Partners](https://shizune.co/investors/profile/globespan-capital-partners) — VC Fund, 3 deals together
- [Pentech Ventures](https://shizune.co/investors/profile/pentech-ventures) — VC Fund, 3 deals together
- [Piton Capital](https://shizune.co/investors/profile/piton-capital) — VC Fund, 3 deals together
- [Vidal Duart Enterprises](https://shizune.co/investors/profile/vidal-duart-enterprises) — VC Fund, 3 deals together

## About Techstars

VC Fund · Boulder, United States

Techstars provides a global platform for early-stage investment and innovation through programs that support startup growth and corporate collaboration. Its services include accelerator programs, startup education initiatives, venture capital funding, and corporate innovation partnerships.The Techstars Mentorship-Driven Accelerator Program offerssupport for startups, while Techstars Startup Programs focus on entrepreneurial education and community building. The Techstars Venture Capital Fund invests in emerging companies, and its Corporate Innovation Partnerships help established brands develop new products and services through collaboration with startups.

5 contacts available at Techstars.

| Name | Title | Profile |
| --- | --- | --- |
| Andrew Cleland | Chief Investment Officer | https://shizune.co/investors/profile/andrew-cleland |
| Artur Hasselbach | Mentor | https://shizune.co/investors/profile/artur-hasselbach |
| Beata Puncevic | Chief Technology Officer | https://shizune.co/investors/profile/beata-puncevic-e5b1 |
| Ben Liao | Managing Director | https://shizune.co/investors/profile/ben-liao |
| Bob Moczydlowsky | Managing Director & Founder, Techstars Music | https://shizune.co/investors/profile/bob-moczydlowsky |

## Similar investors

### Similar stage
- [Antler](https://shizune.co/investors/profile/antler-be9c) — VC Fund
- [Alumni Ventures](https://shizune.co/investors/profile/alumni-ventures-group) — VC Fund
- [General Catalyst](https://shizune.co/investors/profile/general-catalyst-partners) — VC Fund

## FAQ

### What does Andrew Cleland invest in?

Andrew Cleland invests primarily in Software, Machine Learning and Information Technology startups, most often at Series A and Series C stage. Most of the 17 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.

### When did Andrew Cleland last invest?

The most recent investment recorded for Andrew Cleland closed in Jan 2025. Shizune tracks 17 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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