/Companies

LegacyShift

Techstars '22

New York City, US · Founded 2022 · 1 known investors

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LegacyShift is a B2B SaaS platform that automates workplace mentorship and coaching programs using AI/ML and gamification.

Investors · 1

Techstarslisted by TechstarsBoulder · $220K

How we know: the Techstars portfolio · open dataset · Top 3000 Accelerator Startups (no YC) 2026-08 · Not right? Tell us

Company profile

researched Sep 2026

LegacyShift is a business-to-business software-as-a-service platform that automates and streamlines workplace mentorship and coaching programs. The product applies AI/ML and gamification so that organizations can use their existing internal talent to help employees develop new skills, with stated goals of workforce development and retention at scale.

The company positions its offering against two gaps it identifies in the market: internal corporate mentorship that tends to depend on existing personal networks or seniority, and external professional coaching, which it characterizes as expensive and inaccessible to many professionals. It also cites remote work as a factor reducing hands-on support, networking and visibility opportunities for employees.

Founding story

Co-founder and CEO Sandra Appiah Babu-Boateng has said she started the company out of her own experience as an immigrant and Black woman for whom mentorship and coaching were central to career progress, and out of the observation that many professionals, particularly those from diverse backgrounds, never obtain a mentor inside their organization. She and co-founder Isaac previously built what they describe as the largest U.S.-based digital media platform for the Black diaspora community, which scaled to more than 3 million monthly users and worked with enterprises including Prudential, Toyota and State Farm. Together the founders cite over 20 years of combined experience advising companies on DEI and workplace culture and building programs supporting the advancement of multicultural professionals.

Business model

The company sells a SaaS platform to organizations, which deploy it to run internal mentorship and coaching programs for their workforces.

Traction

By December 2022 the company reported having completed Techstars, received coverage in Forbes, and accumulated more than 40 organizations on its waitlist.

▸Full profile — market position, technology, go-to-market, geography, risks & controversies

Market position

LegacyShift positions itself as an alternative to informal, network-dependent internal mentorship and to professional coaching, which it describes as costly and inaccessible for many employees.

Technology

The platform applies AI/ML and gamification to match and support mentorship and coaching relationships and to automate program administration.

Go-to-market

The company has built a waitlist of prospective organizational customers and participated in the Techstars accelerator program; the founders' prior enterprise relationships and DEI advisory background inform its enterprise outreach.

Employers and organizations running workplace mentorship, coaching and talent development programs for their employees.

Geography

United States.

Risks & controversies

The CEO has identified fundraising in a difficult capital market as the company's largest challenge to date.

Compiled by commissioned research from 2 cited public sources — announcements, filings, and press listed under research sources below.

Key figures

latest reported
Organizations on waitlistDec 202240 organizations

Company-reported or press-reported figures, each dated to when it was claimed — not independently audited.

Timeline · 1

launches, deals, and filings
Dec 2022
Completed Techstars accelerator program

The company reported that it had recently completed Techstars, alongside a feature in Forbes.

source ↗

Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.

▸Research sources · 2

primary sources listed

2 public sources were cited for this profile; the first-party ones are listed here.

Frequently asked questions

What does LegacyShift do?
LegacyShift is a B2B SaaS platform that automates workplace mentorship and coaching programs using AI/ML and gamification.
Who are LegacyShift's investors?
LegacyShift's investors include Techstars.
Where is LegacyShift headquartered?
LegacyShift is headquartered in New York City, US.