# Robert Chaplinsky

> Robert Chaplinsky is a Series A investor at Bridgescale Partners backing Software. See 17 investments, check sizes, portfolio and contact details. Updated…

- Type: Angel Investor
- Fund: [Bridgescale Partners](https://shizune.co/investors/profile/bridgescale-partners)
- Location: Menlo Park, United States
- Total investments: 17
- Last investment: May 2021
- Lead investor: 47%
- Last updated: Aug 2026
- LinkedIn: https://www.linkedin.com/in/rchaplinsky
- X (Twitter): https://twitter.com/Bridgescale
- Website: https://x.com/Bridgescale
- Facebook: https://www.facebook.com/rchaplinsky

Robert Chaplinsky is a Series A investor at Bridgescale Partners in Menlo Park focused on Software and SaaS. Rob Chaplinsky is the Co-Founder and Managing Director Link Ventures. Rob previously worked at Bridgescale Partners as the Managing Director. He Harvard Business School and the University of Waterloo.

## Contacts

5 contacts available for Robert Chaplinsky: work email, personal email, work phone, personal phone and socials. Sign up free to unlock them: https://app.shizune.co/sign-up/investor-profiles/find-email/robert-chaplinsky?utm_source=investor_profile

## Round sizes

| Stage | Round size |
| --- | --- |
| Seed | $1.6M–$1.6M |
| Series A | $3.5M–$9.7M |
| Series B | $15M–$50M |

## Investment focus

### Industry

| Industry | Investments | Share |
| --- | --- | --- |
| Software | 4 | 24% |
| SaaS | 3 | 18% |
| Sales | 3 | 18% |
| FinTech | 2 | 12% |
| E-Learning | 2 | 12% |

32 industries tracked in total.

### Stage

| Stage | Investments | Share |
| --- | --- | --- |
| Series A | 4 | 24% |
| Seed | 3 | 18% |
| Series B | 3 | 18% |
| Series C | 2 | 12% |
| Series F | 2 | 12% |

7 stages tracked in total.

### Country

| Country | Investments | Share |
| --- | --- | --- |
| United States | 5 | 29% |
| Canada | 4 | 24% |

## Investments

| Company | Description | Amount | Stage | Date | Website |
| --- | --- | --- | --- | --- | --- |
| Caribou | MotoRefi is an auto refinance startup that helps customers to save on their car loan. Through partnerships with top local and community lenders, the company brings customers great rates and lower monthly payments, ultimately saving customers an average of $100 per month on their car payments.Its secure, digital platform makes it easy forcustomers to see exactly how much they can save and complete the refinance process quickly, all from the comfort of their home. What's more, MotoRefi does all the heavy lifting, including paying off the old lender as well as retitling the vehicle, saving the customers those dreaded trips to the DMV.MotoRefi was founded in 2016 and is based in Arlington, Virginia. | $50M | Series B | May 28, 2021 | https://www.motorefi.com/ |
| Trust & Will | Trust & Will is an online service providing legal forms and information that makes creating estate planning easy, fast, and secure. It is not a law firm and is not a substitute for a lawyer’s advice about complex estate planning. The company is backed by some venture capital firms including Revolution’s Rise of the Rest, Western TechnologyInvestments, Luma Launch, Halogen Ventures, and Techstars, as well as angel investors.Trust & Will was founded in 2017 and is headquartered in San Diego, CA. | $15M | Series B | Nov 17, 2020 | https://www.trustandwill.com |
| Uvaro | Uvaro's career success platform includes training, paid experience, advancement and ongoing coaching to ensure long-term career success. Our training program includes on-demand and live classes, our virtual internships let companies hire talent based on performance, our coaching and mentorship network drive ongoing career growth. Our averagestudent lands their new role in less than 17 days from graduation at more than 2x their previous income, and in their new roles achieve 50% more sales than their peers. | $1.6M | Seed | Sep 01, 2020 | https://uvaro.com/ |
| Uvaro | Uvaro's career success platform includes training, paid experience, advancement, and ongoing coaching to ensure long-term career success. Their training program includes on-demand and live classes. Their virtual internships let companies hire talent based on performance. Their coaching and mentorship network drive ongoing career growth. | $1.6M | Seed | Sep 01, 2020 | https://kiite.ai |
| Caribou | MotoRefi is an auto refinance startup that helps customers to save on their car loan. Through partnerships with top local and community lenders, the company brings customers great rates and lower monthly payments, ultimately saving customers an average of $100 per month on their car payments.Its secure, digital platform makes it easy forcustomers to see exactly how much they can save and complete the refinance process quickly, all from the comfort of their home. What's more, MotoRefi does all the heavy lifting, including paying off the old lender as well as retitling the vehicle, saving the customers those dreaded trips to the DMV.MotoRefi was founded in 2016 and is based in Arlington, Virginia. | $9.4M | Series A | Feb 14, 2020 | https://www.motorefi.com/ |
| Trust & Will | Trust & Will is an online service providing legal forms and information that makes creating estate planning easy, fast, and secure. It is not a law firm and is not a substitute for a lawyer’s advice about complex estate planning. The company is backed by some venture capital firms including Revolution’s Rise of the Rest, Western TechnologyInvestments, Luma Launch, Halogen Ventures, and Techstars, as well as angel investors.Trust & Will was founded in 2017 and is headquartered in San Diego, CA. | $6M | Series A | Dec 17, 2019 | https://www.trustandwill.com |
| Pomelo Health | Pomelo Health was founded in 2012, with the mission of liberating patients from clinic waiting rooms and providing better access to healthcare. We were named one of the twenty-five most innovative businesses by C2-MTL. We are now leaders in digital healthcare management through our suite of products enabling full-circle appointment management forclinics and patients alike. In the past year alone, we’ve serviced 12 million users through our network of clinics across North America that use our products.We believe healthcare access should be more than a regular service: it should be a trustable, an easy to use and a practical tool for patients and clinics. Our ambition is not only about helping people or simply creating another ingenious app for them. We want to revolutionize the experience for both patients and clinics, to gain their trust, and to change their perception about healthcare services.At Pomelo Health, the driving force behind everything we do is our unwavering drive to improve patient and clinic staff experiences and that's the best part of our work! We are proud of all that we have achieved, but most of all, we are excited and inspired by the adventures to come. | $3.5M | Series A | Jul 11, 2017 | https://www.pomelohealth.com/ |
| Xactly | Xactly is a leading global provider of enterprise cloud-based Sales Performance Management solutions for planning and incenting sales organizations, including sales quota and territory planning, incentive compensation management, and predictive analytics. Xactly Incent Suite drives sales behaviors to align with company objectives, increasingemployee trust and loyalty with error-free commission payments and on-demand visibility, improving operational efficiencies and productivity. | $12M |  | Dec 01, 2014 | http://www.xactlycorp.com |
| Axonify | Axonify provides eLearning software, interval reinforcement solutions, and gamified learning. Using principles of interval reinforcement and incorporating the realities of how emerging workforces learn in today’s environment, Axonify enables its customers to make training stick and improve employee performance. |  | Seed | Mar 06, 2012 | http://www.axonify.com |
| Xactly | Xactly is a leading global provider of enterprise cloud-based Sales Performance Management solutions for planning and incenting sales organizations, including sales quota and territory planning, incentive compensation management, and predictive analytics. Xactly Incent Suite drives sales behaviors to align with company objectives, increasingemployee trust and loyalty with error-free commission payments and on-demand visibility, improving operational efficiencies and productivity. | $12M | Series F | Aug 03, 2010 | http://www.xactlycorp.com |

10 of 17 investments shown.

## Co-investors
- [Motley Fool Ventures](https://shizune.co/investors/profile/motley-fool-ventures) — VC Fund, 4 deals together
- [Icon Ventures](https://shizune.co/investors/profile/iconventures) — VC Fund, 3 deals together
- [Xfund](https://shizune.co/investors/profile/xfund) — VC Fund, 3 deals together
- [Accomplice](https://shizune.co/investors/profile/accomplice-atlas-venture) — VC Fund, 2 deals together
- [BDC Capital’s Women in Technology Venture Fund](https://shizune.co/investors/profile/bdc-capital-s-women-in-technology-venture-fund) — VC Fund, 2 deals together
- [Techstars Ventures](https://shizune.co/investors/profile/bullet-time-ventures) — VC Fund, 2 deals together

## About Bridgescale Partners

VC Fund · Menlo Park, United States

Bridgescale Partners is a growth equity and venture capital firm that invests in technology companies. It is based in Menlo Park, California.

1 contacts available at Bridgescale Partners.

| Name | Title | Profile |
| --- | --- | --- |
| Debbie Quement | CFO | https://shizune.co/investors/profile/debbie-quement-ab37 |

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## FAQ

### What does Robert Chaplinsky invest in?

Robert Chaplinsky invests primarily in Software, SaaS and Sales startups, most often at Series A and Seed 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.

### What is Robert Chaplinsky's check size?

Robert Chaplinsky typically joins rounds of $1.6M–$1.6M at Seed, $3.5M–$9.7M at Series A and $15M–$50M at Series B. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Robert Chaplinsky participates in.

### How do I contact Robert Chaplinsky?

Public channels for Robert Chaplinsky include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.

### When did Robert Chaplinsky last invest?

The most recent investment recorded for Robert Chaplinsky closed in May 2021. 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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