Darrell Rosenstein — Business Development Executive

Most companies don’t fail to hire strong GTM leaders. They fail to hire them at the right moment, with the right mandate. I work with CEOs, boards, and investors of SaaS, commerce, and AI-native companies at inflection points — typically when the product is proven, growth is real, and founder-led GTM systems begin to strain. Across these transitions, the most common problem isn’t talent. It’s misalignment between what the business needs next and what the role is designed to do. Over the last 29 years, I’ve helped companies navigate this shift by clarifying: whether the organization needs execution, architecture, or both how GTM leadership should evolve as scale and complexity increase how to reduce leadership churn caused by premature or mismatched hires The result is materially better outcomes. Our clients see ~65% improvement in executive retention, because hires are made with mandate clarity, cultural alignment, and behavioral fit — not urgency alone. Representative Operating Experience My background includes senior GTM and revenue leadership roles across growth stages: Seed-stage eCommerce search platform: First sales hire; closed first 3 enterprise deals, generated $1.75M in 12 months, built initial sales team Series A retail AI company: Head of Strategic Accounts; closed $4.5M in 18 months Series A B2B commerce platform: VP of Sales; scaled team from 5 to 9 in 3 months, exceeded revenue targets by 40% Seed-stage retail pricing company: CEO; raised $9M Series A and personally closed $2.5M in first 12 months Series C composable CMS provider: Division VP of Sales; led region from last to top-performing ($8M ARR) in 12 months Series B composable DXP provider: CMO; increased qualified pipeline 300% in 8 months and accelerated competitive positioning across analyst rankings This operating context informs how I advise leadership teams today — particularly around CRO, CCO, CMO, Product, and Customer leadership transitions. Client Experience I’ve worked with a broad set of commerce, MarTech, and enterprise platforms, including: Bloomreach, Elastic Path, Demandware, Hybris, Sitecore, RichRelevance, Riversand, Model N, RELEX, SAS, OpenTable, Pivotree, Profitlogic, and others. I’m not involved when companies want “a CRO because it’s time.” I am involved when leadership wants to get the decision right.

Stackforce AI infers this person is a GTM leadership expert in SaaS and commerce sectors.

Location: Seattle, Washington, United States

Experience: 31 yrs 3 mos

Skills

Material Requirements Planning (mrp)
Production Management
Executive Sales Recruitment
Executive Search
Business Development

Career Highlights

Expert in GTM leadership transitions for SaaS and commerce.
Achieved 65% improvement in executive retention.
Proven track record in scaling revenue leadership teams.

Work Experience

Decision Flow, LLC

Commercial Growth Director (4 mos)

UpStart Commerce

Advising Board Member (1 yr 10 mos)

Intrinsic Executive Search

Director-Americas (3 yrs 6 mos)

CLEAR Financial Technologies, Inc.

Board Member and Investor (10 yrs 9 mos)

The Rosenstein Group

Principal (12 yrs 11 mos)

Managing Partner (22 yrs 11 mos)

Hall Kinion

Branch Manager (4 yrs 7 mos)

Strategic Staffing Solutions

National Director, Permanent Placement Services (8 mos)

Robert Half International

Division Director (3 yrs 7 mos)

Education

BA at University of Vermont

Diploma at Hanover High School

Darrell Rosenstein

Business Development Executive

Seattle, Washington, United States31 yrs 3 mos experience

Most Likely To SwitchHighly Stable

Key Highlights

Expert in GTM leadership transitions for SaaS and commerce.
Achieved 65% improvement in executive retention.
Proven track record in scaling revenue leadership teams.

Stackforce AI infers this person is a GTM leadership expert in SaaS and commerce sectors.

Contact

darrell@rosensteingroup.com LinkedIn

Skills

Core Skills

Material Requirements Planning (mrp)Production ManagementExecutive Sales RecruitmentExecutive SearchBusiness Development

Other Skills

Aerospace ManufacturingPredictive AIProduction Planningexecutive marketing recruitmentStart-upsSales ManagementStart-up ConsultingStart-up VenturesLead GenerationHuman Capital ManagementPersonality AssessmentMarketing AutomationPricingForecastingRisk Management

About

Experience

31 yrs 3 mos

Total Experience

7 yrs

Average Tenure

22 yrs 11 mos

Current Experience

Decision flow, llc

Commercial Growth Director

Jan 2026 – Present · 4 mos · Seattle, Washington, United States · Remote

Decision Flow delivers what every MRP system wishes it could do—real-time, dynamic re-planning after orders are released.
Production Manager, our digital‑twin‑powered product, replaces manual scheduling with predictive flow intelligence. It integrates directly with your MRP to forecast disruptions, identify emerging constraints, and automatically synchronize production in real time. Production Manager optimization engine is driven by a secure, proprietary AI model. We help mid-market Aerospace and Defense and discreet industrial manufacturers boost output while lowering operating costs. Customers use our flow‑optimization platform to cut inventory by up to 40%, shorten lead times by up to 30%, and increase on-time delivery by up to 20%, all without adding labor or capital equipment. Reported ROI is less than one year.
Our platform blends deep industry expertise with advanced modeling, predictive analytics, and simulation to improve execution, resilience, and competitive advantage. Stop reactive spreadsheet resolutions and start proactively optimizing your post release processes.
My mission is simple: help businesses identify and eliminate the barriers in their supply chain and production processes that prevent them from hitting their strategic targets.

Material Requirements Planning (MRP)Aerospace ManufacturingPredictive AIProduction ManagementProduction Planning

Upstart commerce

Advising Board Member

Jan 2024 – Nov 2025 · 1 yr 10 mos · Manchester, New Hampshire, United States · Remote

Upstart is the developer of NoChannel Commerce a fully composable MACH B2C commerce platform. Our platform combines the power of omnichannel retailing, advanced inventory management, personalized customer experiences, and robust analytics to help you thrive in today’s competitive landscape. Streamline operations, increase sales, and drive customer loyalty with our comprehensive suite of retail solutions.

Intrinsic executive search

Director-Americas

Dec 2016 – Jun 2020 · 3 yrs 6 mos · Seattle Washington and London, England

Intrinsic Executive Search provides sales leadership to SaaS Martech, AI, Cloud and ECommerce firms expanding in Europe and The Americas. Our business is to assist software sales and marketing pioneers to best utilize their experience, clients,network and vision in new, disruptive solution arenas.
We represent professionals who have demonstrated expertise in driving new business for large complex enterprise software applications. These professionals will have pioneered relationships with the sales and marketing line of business leadership for their respective clients.
They will have distinguished themselves in the introduction and evangelization of new product offerings, development of processes, go-to-market messaging and strategy, development of territory and compensation plans, hiring, on-boarding, and training of teams, partnership and business development with ISV, Channel and Service Providers, corporate development, strategy, and fund raising.

Clear financial technologies, inc.

Board Member and Investor

Aug 2015 – Present · 10 yrs 9 mos · Heber City, Utah, United States / St Thomas USVI

CLEAR is a mobile first web portal that provides financial information and tools to currency traders and bona fide hedgers (primarily exporters of goods and services) around the world through it's web-based, multi-language platform. This suite of informational tools is unprecedented. It is offered at a price that is affordable by even the smallest company or individual trader, yet valuable to the largest of companies and institutions. This combination of information, tools and price is a true global game-changer in the largest market on Earth.

Executive Sales RecruitmentStart-up ConsultingStart-up VenturesBusiness DevelopmentLead Generationexecutive marketing recruitment+2

The rosenstein group

2 roles

Principal

Jan 2004 – Dec 2016 · 12 yrs 11 mos

Founded and built a boutique executive search practice focused on sales, marketing, and revenue leadership for SaaS platforms and systems integrators serving retail and B2C markets.
During this period, I partnered closely with founders and early investors to:
establish initial GTM leadership teams
scale commercial organizations post–product-market fit
support revenue leadership through growth, restructuring, and acquisition
This work laid the foundation for my current advisory focus on leadership transitions at scale.

Managing Partner

Jun 2003 – Present · 22 yrs 11 mos

I advise CEOs, boards, and private equity sponsors on GTM leadership transitions across SaaS, commerce, MarTech, supply chain, and analytics companies — typically at moments when growth is real, complexity is rising, and founder-led systems begin to strain.
Over the last two decades, I’ve worked with 170+ SaaS organizations to design and execute senior GTM hires, including CRO, CCO, CMO, Product, and Customer leadership roles. My focus is less on filling roles and more on helping leadership teams clarify timing, mandate, and fit before the hire is made.
Because I’ve operated inside these businesses myself, I bring practical context to board-level decisions — particularly where execution, architecture, and organizational readiness are misaligned.
Representative clients include:
Marketlive, Demandware, Hybris, Bloomreach, Elastic Path, Sitecore, Flow Commerce, RichRelevance, Riversand, RELEX, SAS, OpenTable, and other commerce and enterprise platforms.

Executive Sales Recruitmentexecutive marketing recruitmentExecutive SearchStart-upsSales Management

Hall kinion

Branch Manager

May 1999 – Dec 2003 · 4 yrs 7 mos · San Francisco Bay Area

As manager, served as the player/coach for the technology and sales and marketing teams for the San Francisco, Larkspur and Novato offices of Hall Kinion. Responsible for hiring, training and leading the teams as well as the development an delivery of educational materials, regional and national training conferences, public addresses and appearances on TechTv as well as regional trade shows.
Exceeded quota by 50%, 500%, 50% and 75% successively during tenure
Ranked in top 1% of 400 recruiters worldwide
Multiple award winner and club winner
Member of #2 office Worldwide
Evaluation committee for SFA task force
Pioneer of vertical marketing strategy and practices for this regionally focused firm

Strategic staffing solutions

National Director, Permanent Placement Services

Sep 1998 – May 1999 · 8 mos

Developed and executed the first permanent direct hire initiative for this hi technology business consulting firm. This included the development of territory plans, client evaluations, business case analysis, training materials, business procedures manuals, field training, client development, account management and account development for 7 offices in 6 states employing over 50 professionals and 400 consultants. Established office and grew business in California.