# Katherine Caldwell

> Katherine Caldwell is a seed investor at TwentyTwo VC backing Software and FinTech. See 13 investments, check sizes, portfolio. Updated Aug 2026.

- Type: Angel Investor
- Fund: [TwentyTwo VC](https://shizune.co/investors/profile/twentytwo-vc)
- Location: San Francisco, United States
- Total investments: 13
- Last investment: Sep 2024
- Lead investor: 0%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/katherinenilan/
- Website: http://twentytwo.vc

Katherine Caldwell is a seed investor at TwentyTwo VC in San Francisco focused on Software and FinTech. Katey Caldwell is the Founder and General Partner of Twenty Two Ventures.

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 6 | 46% |
| FinTech | 3 | 23% |
| Financial Services | 3 | 23% |
| Apps | 2 | 15% |
| Banking | 2 | 15% |

33 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Seed | 9 | 69% |
| Pre-Seed | 2 | 15% |
| Series A | 2 | 15% |

### Country

| Country | Investments | Share |
| --- | --- | --- |
| United States | 9 | 69% |
| France | 1 | 8% |
| Mexico | 1 | 8% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Cheers | Cheers is the control center for your frontline brand, answering three critical questions: 1. What's our reputation? 2. Who's driving it? 3. How do we improve it?Most tools stop at “what.” Without “who,” “how” is guesswork.Our AI-powered platform creates the first real-time dataset that attributes online reviews, social mentions,loyalty sign-ups, and NPS surveys directly to individual frontline employees. Instead of vague aggregate reports, managers get clear, actionable insights: who to coach, who to recognize, and which actions actually work.As AI-driven search and agents weigh every public signal, your brand is judged everywhere. Cheers monitors and attributes those signals so you can actually do something about it.Vivint Smart Home identified top performers and generated 65,000+ new five-star reviews in five months across 400 locations. | $835K | Pre-Seed | Sep 25, 2024 |  |
| Vista Power | Vista Space creates Tesla-inspired modular structural battery packs for spaceships. | $982.5K | Pre-Seed | Apr 30, 2024 |  |
| Pirros | Engineers and Architects end up redesigning hundreds of details a year just because they are unable to search through all their past details. Pirros allows them to effectively manage and search all their past project details so that they can find reasonable starting points rather than starting from scratch. | $2M | Seed | Aug 31, 2023 |  |
| Palette | Palette develops a sales compensation software that helps companies easily create, manage, and automate compensation plans. Palette creates and maintains efficient compensation plans built for company growth and goals. | $6M | Seed | May 18, 2022 |  |
| Finley Technologies | Finley simplifies debt capital raise and management. Finley's software helps growing companies automate due diligence, ensure compliance, and streamline ongoing reporting with their capital providers. Customers like Ramp rely on Finley to manage hundreds of millions in debt capital from capital providers. The Finley team brings experience fromGoldman Sachs, Nova Credit, and Palantir Technologies, and is backed by Y Combinator and Bain Capital Ventures. | $3M | Seed | Jun 14, 2021 |  |
| Lendflow | Lendflow develops a lending infrastructure platform built to change and improve the way businesses access capital. They allow a user to embed financial products into their software to increase engagement, improve retention, and become a source of capital for their business users. They also provide term loans, lines of credit, and invoice factoringto cover businesses of all sizes and credit risks, enabling construction, home services companies, e-commerce, restaurants, transportation, and fitness businesses to connect their users with capital and increase the reach of their businesses. | $2.7M | Seed | Apr 10, 2021 |  |
| PointCard | Point Card offers rewards, including additional cash-back on go-to subscriptions like Netflix, Spotify, HBO Max, Hulu, and more. It features an advanced chipset for secure payments, a high-tensile synthetic polymer construction, and comes in your choice of four editions. It was launched in 2018 and is headquartered in San Francisco, California. | $10.5M | Series A | Jul 01, 2020 |  |
| Point Card | Point Card offers rewards, including additional cash-back on go-to subscriptions like Netflix, Spotify, HBO Max, Hulu, and more. It features an advanced chipset for secure payments, a high-tensile synthetic polymer construction, and comes in your choice of four editions. It was launched in 2018 and is headquartered in San Francisco, California. | $10.5M | Series A | Jul 01, 2020 |  |
| Aesthetic | Aesthetic's mission is to make the world more well designed by giving every business creative superpowers. To do this, we're automating all the production design work needed by companies, starting with social media graphics. Social media is an important marketing channel for businesses, but creating quality content is hard. Our productcreates the social marketing posts your brand needs without doing any design work. | $3.1M | Seed | Apr 28, 2020 |  |
| Nexu | Nexu is a financing platform used by car dealerships to offer to finance to more car buyers in a 100% digital and real-time experience. Nexu's platform uses AI, statistical algorithms, and technology automation. | $1.6M | Seed | Mar 18, 2020 |  |

10 of 13 investments shown.

## Co-investors
- [Y Combinator](https://shizune.co/investors/profile/y-combinator) — VC Fund, 9 deals together
- [Restive](https://shizune.co/investors/profile/financial-venture-studio) — VC Fund, 4 deals together
- [Kindred Ventures](https://shizune.co/investors/profile/kindred-ventures-2) — VC Fund, 4 deals together
- [Liquid 2 Ventures](https://shizune.co/investors/profile/liquid2-ventures) — VC Fund, 4 deals together
- [Bain Capital Ventures](https://shizune.co/investors/profile/bain-capital-ventures) — VC Fund, 3 deals together
- [2048 Ventures](https://shizune.co/investors/profile/2048-ventures) — VC Fund, 2 deals together

## About TwentyTwo VC

VC Fund · San Francisco, United States

TwentyTwo VC is an early-stage venture capital firm dedicated to investing in a new generation of companies tackling our present and future quality of life.TwentyTwo VC are composed of active investors, investing in people and companies doing great things. We make early-stage investments in companies typically post-launch, pre-seed, seed. We arelooking for companies that are solving for quality of life, bringing something new to the table, and executing scalable business models. Beyond that, we seek magnetic, tenacious, adaptable founders who aren’t afraid of the big ideas and ultimately ship great things.

1 contacts available at TwentyTwo VC.

| Name | Title | Profile |
| --- | --- | --- |
| Katherine Caldwell | Managing Partner | https://shizune.co/investors/profile/katherine-nilan |

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## FAQ

### What does Katherine Caldwell invest in?

Katherine Caldwell invests primarily in Software, FinTech and Financial Services startups, most often at Seed and Pre-Seed stage. Most of the 13 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 Katherine Caldwell last invest?

The most recent investment recorded for Katherine Caldwell closed in Sep 2024. Shizune tracks 13 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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