GTM leadership decisions that hold
About The Rosenstein Group
The Rosenstein Group helps B2B SaaS companies make GTM leadership decisions that hold.
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.
Who we are
We combine leadership advisory, external talent intelligence, and retained executive search to help CEOs, founders, boards, and investors understand what the business actually needs before deciding who should fill the role.
For 30 years, we have worked in the markets we know deeply: MarTech, eCommerce, Composable Commerce, Supply Chain SaaS, and Enterprise AI.
We do not fill jobs. We build mandates.
The seat is rarely the whole problem
An open position is visible. The underlying leadership problem often isn't.
The commercial plan may have changed. The sales motion may have changed. A company may be moving upmarket, entering a new geography, launching a new category, or preparing for its next stage of growth. The leadership team that got the business here may not be the leadership team required for what comes next.
That is why we do not begin with a job description. We begin with the mandate.
What must this leader accomplish? What kind of commercial motion will they inherit? What does the existing team need from them? Which experience actually transfers? Where is the organization vulnerable? And what would make an otherwise impressive executive fail?
Only then do we determine what leadership decision the business should make.
Why TRG
Thirty years of domain depth.
We have spent three decades inside the markets we serve. That history gives us context a generalist firm cannot develop during a search. We know the companies, the categories, the talent markets, and the commercial patterns that have shaped successive generations of B2B software. More importantly, we understand how those patterns change. The executive who succeeds in one environment may struggle in another, even when the companies appear similar on paper.
Motion matters more than logos.
A successful enterprise AE from a household-name software company is not automatically the right AE for a Series A company. The logo may be impressive. The sales motion may be completely wrong. We establish the motion before we build the candidate profile: customer, deal complexity, sales cycle, organizational maturity, resources, competitive environment, and what the individual will actually have to create rather than inherit. We recruit for the environment the person is entering, not simply the résumé they are leaving.
External intelligence changes the decision.
Internal reporting tells you what has already happened inside your company. External talent intelligence tells you what is happening around it. How does the market perceive your company? Where is the strongest relevant talent? What are competitors building? How receptive is the talent market to your opportunity? What does your opportunity look like to the people you most want to attract? Three decades of conversations outside the walls of any single company give TRG a perspective an internal team cannot easily reproduce.
Mandates, not job descriptions.
Leadership searches can go wrong before the first candidate is interviewed. If the company has not defined the commercial mandate, success criteria, operating environment, and likely failure modes, even an exceptional candidate can become the wrong hire. We build that context first. The objective is not to produce candidates who match a specification. It is to understand what success requires and then find the people capable of delivering it.
Cognitive fit, not just credentials.
Experience tells you what someone has done. It does not necessarily tell you how they instinctively approach problems, uncertainty, structure, risk, or execution. Kolbe, a licensed third-party instrument, assesses conative fit: the instinctive approach to problem-solving and execution that résumés and interviews do not reveal. It is one input into a human decision, not a substitute for one.
| Dimension | Typical search firm | TRG |
|---|---|---|
| Starting point | A job description | A mandate: business context, first-year outcomes, failure modes, agreed before recruiting starts |
| Diligence on the existing team | Usually folded into the search, or not offered | Fee-separated — Leadership Due Diligence is never a setup for a sale |
| Domain focus | Generalist, broad industry coverage | MarTech, eCommerce, Composable Commerce, Supply Chain SaaS, and Enterprise AI only, for 30 years |
| Candidate fit signal | Resume and interview alone | Resume, interview, and a licensed Cognitive Fit Assessment (Kolbe) as one input to a human decision |
| Credentials | Varies | The only executive recruiter ever admitted to the MACH Alliance |
Sometimes the answer isn't a search
A leadership problem does not automatically require a new leader.
We help CEOs, boards, founders, and investors understand the team already in place, the mandate the business now requires, and the external talent market before deciding whether to hire, develop, restructure, or wait.
That work can include Leadership Due Diligence, Competitive Talent Intelligence, the GTM Leadership Readiness Assessment, or Retained Executive Search.
The engagement changes. The fundamental question does not: what leadership decision gives this company the best chance of carrying its commercial plan?
Evidence over promises
We measure our work because leadership decisions should produce outcomes beyond an accepted offer. Historically:
500+
GTM placements across 170+ SaaS clients
1 in 4
Submittals historically hired
Two-year placement retention
Repeat client rate
25% of placements promoted within two years.
The only executive recruiter ever admitted to the MACH Alliance.
These are measured historical results, not guarantees of future outcomes.
Demandware: leadership decisions visible years later
During Demandware's commercial build, The Rosenstein Group made 16 executive placements across the organization.
When Salesforce acquired Demandware for 2.8 billion dollars in 2016, TRG placements delivered 27% of Demandware's market cap at acquisition. Five of those executives became multi-millionaires in the transaction.
The point is not that a search firm created Demandware's value. It is that the people a company chooses can participate in creating extraordinary value, and leadership decisions made years earlier can still be visible in the outcome.
Our client history also includes Vendavo, where TRG completed 13 placements across sales, services, and product in 60 days, as well as SAP Hybris, Bloomreach, Elastic Path, and Narvar.
In a client's words
“I have been a client of Darrell’s for approximately 14 years, initially as COO of Demandware and later as CEO of the Salesforce Commerce Cloud. He is the consummate professional...conscientious and reliable. Darrell understood our industry and our company very well, and it showed in the results. He nearly always delivered with relevant, high quality talent. In the early pioneering days of Demandware, Darrell helped me to find one of our very first sales leaders on the west coast (perhaps our most reliable producer over the years). Later, as we became a larger public company, Darrell became a key partner in scaling our team with high quality talent amidst a highly competitive environment. Without exceptional business partners like Darrell, we wouldn’t have been able to attract the talent. Thank you🙏”
Jeffrey Barnett, former COO of Demandware and former CEO of Salesforce Commerce Cloud
MarTalks keeps us in the conversation
MarTalks is our podcast, built around the people shaping the markets we serve.
Each appearance is designed first for the guest. A conversation becomes usable commercial content: quotable segments, video, and clips their teams can put to work in sales and marketing.
For TRG, those conversations have a useful side effect. They keep us close to how founders, CEOs, operators, and investors are thinking about markets, growth, technology, talent, and the problems emerging before they become job descriptions.
That continuing conversation is part of how we stay connected to the markets in which we advise our clients.
Meet Darrell Rosenstein
Darrell Rosenstein
Founder and Managing Partner
Every day I have the privilege of connecting extraordinary people to meaningful work, and watching them realize their potential by helping others succeed.
Darrell Rosenstein has placed go-to-market professionals in B2B software since 2000, building leadership networks across successive generations of MarTech, eCommerce, Composable Commerce, Supply Chain SaaS, and Enterprise AI.
He has completed more than 500 GTM placements for more than 170 SaaS companies, from Seed through pre-IPO.
His client history includes Demandware, SAP Hybris, Bloomreach, Elastic Path, Vendavo, Narvar, and other companies that have helped define their categories.
Darrell is trained in the Kolbe Method, hosts MarTalks, and serves on the board of Upstart Commerce.
darrell@rosensteingroup.com | LinkedIn: linkedin.com/in/darrellrosenstein
Facing a GTM leadership decision?
Before you write the job description, define the mandate. Talk with Darrell about what the business needs next.