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The Rosenstein Group

Leadership Advisory · Retained Executive Search

Leadership decisions that hold.

The Rosenstein Group works with CEOs, founders, boards, and VC, PE, and growth equity investors at Series A to pre-IPO B2B SaaS companies in MarTech, eCommerce, Composable Commerce, Supply Chain SaaS, and Enterprise AI.

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GTM leaders our clients have hired through TRG

GTM leaders our clients have hired through TRG

500+

GTM placements

Including 16 executive placements for Demandware.

170+

SaaS clients, from Seed to pre-IPO

85%+

repeat client rate

Internal data explains yesterday. External intelligence predicts tomorrow.

I'm a founder or CEO hiring

Retained search and leadership advisory for your next GTM hire.

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I'm an investor

Due diligence, readiness assessment, and search for portfolio companies.

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I'm a candidate

See the roles TRG places and how to get on our radar.

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Our clients

What it is. A leadership advisory firm that also delivers retained executive search. Search is one implementation capability, not the business model.

Who it's for. CEOs, founders, boards, and investors at Series A to pre-IPO B2B SaaS companies in MarTech, eCommerce, Composable Commerce, Supply Chain SaaS, and Enterprise AI.

What it delivers. Leadership decisions that hold: the right GTM leaders, and an honest read on the teams already in the seat.

We build the mandate before we build the slate.

  1. 1

    The mandate.

    Business context, first-year outcomes, failure modes, the team to be built, and board expectations, agreed before recruiting starts.

  2. 2

    Motion before profile.

    We define how this role must sell, market, or serve before deciding who could do it.

  3. 3

    Short slates.

    We submit short. Volume submission moves the screening burden onto your calendar, and executive attention is the scarcest thing you have.

  4. 4

    After the hire.

    Structured check-ins through the first months, so issues surface while they are still easy to fix.

Cognitive Fit Assessment.

Kolbe, a licensed third-party instrument, gives a read on how a candidate instinctively approaches problems and execution. It is one input to a human decision, never a screen or a cutoff.

Human judgment throughout.

Every advancement decision is made by a person.

Retained Executive Search

How we help

Leadership advisory

Leadership Due Diligence

Due diligence on people. An independent, written assessment of whether a management team can carry the investment thesis or strategic mandate, for boards, CEOs, and investors in B2B software.

GTM Leadership Readiness Assessment

An independent read on whether your go-to-market leadership team has the coverage, clarity, and alignment to carry the plan.

Competitive Talent Intelligence

Outside-in intelligence on your commercial leadership. Confidential conversations with the market show how it sees your leadership team, where your exposure sits, and what the evidence can and cannot support.

Retained executive search

Retained Executive Search

Retained search for key GTM positions at Series A to pre-IPO B2B SaaS companies. We build the mandate before we build the slate.

Kolbe Profiling

A Cognitive Fit Assessment add-on for clients inside a live search. Kolbe, a licensed third-party instrument, shows how a candidate instinctively takes action, read against your own team.

Recruiting Training

For VC portfolio companies reducing external spend on mid-level GTM roles. Your teams learn the method behind The Rosenstein Retained Search Methodology, so they can run those hires themselves.

AI Talent Partner

We run the search for your key GTM positions up to your interview stage. You interview finalists. AI speeds up the market mapping, and a person makes every advancement decision.

Fractional Talent Partner

A trained TRG sourcer embedded in your hiring, built around personal daily video outreach, for companies with continuous GTM hiring across multiple roles at once.

GTM Talent Excellence

We do not replace your recruiters. We teach them to recruit this industry, so your team can hire GTM people from individual contributor through second-line manager with the discipline TRG applies to its own searches.

Complimentary Offers

Four ways to get real value from TRG before any engagement. Complimentary, always, and never a trade for a mandate.

What clients say

“For go-to-market hires, first, you have to define what experience you want to deliver to customers. Second, you assess whether a candidate can deliver that experience -- ideally in ways you never even imagined. Third, you confirm that your company can provide that candidate the challenge and opportunity she/he seeks. … Darrell understands all of these steps.”
Michael McCarroll, client
“Given the strength of his network, it's clear why so many retail software companies trust him with executive searches. Darrell doesn't just know the key players; he understands the nuances of the retail tech business and exactly what's required to succeed, no matter the category or niche.”
Nathaniel Fry, client
“Darrell's knowledge and connections in the MarTech world were extremely helpful from securing a board member to identifying and approaching alliance partners to formulating business strategy. He is a true asset to any startup founder”
Zohar Hod, client

MarTalks Podcast

One conversation. Content you can keep using.

Founders, CEOs, and operators shaping B2B software talk through what they are building and what they see in the market, and leave with content their teams keep using. Hosted by Darrell Rosenstein, with 12,000 total listeners across all episodes.

Explore the podcast