Head of Forward Deployed Services

Madrona Venture Labs

San Francisco (CA)

On-site

USD 160,000 - 220,000

Full time

14 days+

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Benefits offered by this job

Competitive salary + equity

Premium medical, dental & vision

401(k), immediate eligibility

Lunch in-office 5 days/week

Flexible/unlimited PTO

Commuter stipend

Wellness stipend

Parental leave

Relocation assistance

In-office culture in San Francisco

Job summary

DOSS is seeking a senior leader to own the end-to-end post-sales lifecycle for our largest clients and to scale the PMO function as we move upstream into upper mid-market and enterprise.

In this player-coach role you’ll manage strategic accounts and build the capabilities that accelerate adoption, with cross-functional collaboration across Sales, Product, and Engineering, including embedded engineers on customer sites.

Qualifications

10+ years in professional services, consulting, operations, or product operations at a technology company.
Experience managing and developing a team.
Familiarity with forward deploy or embedded engineering models, where technical resources operate directly in customer environments to drive adoption and accelerate time-to-value.
Systems thinker. Our business is highly interconnected across people, process, and technology.

Responsibilities

Own the customer lifecycle across discovery, product design, build, UAT, and go-live for complex accounts.
Lead and develop the PMO team, set standards, drive calibration, and foster ownership.
Build new product capabilities as Doss expands to enterprise customers, acting as operator and product thinker.
Set the standard for how the team works, including best practices, process improvements, and tooling decisions.
Partner cross-functionally with Sales, Product, and Engineering, including forward deploy engineers, to map workflows and drive data migrations.
Drive AI-native operations to improve delivery speed and quality across the team.

Skills

Leadership experience

Systems thinking

Analytical skills

Customer obsession

High-pressure environments

Tools

SQL

Job description

About Doss

DOSS is building an Operations Cloud for the real world.

A modern, AI-native platform for physical product businesses to manage the flow of goods, dollars, and data in real time, across:

Procurement
Inventory
Orders
Fulfillment
Finance

Built to replace spreadsheet chaos and rigid, consultant-heavy ERPs. Fast time-to-value, adaptable as the business evolves.

Through our Adaptive Resource Platform (ARP) and unified operational data model, teams deploy quickly, automate workflows, and make changes without months of re-implementation.

We recently raised a $55M Series B, co-led by Madrona and Premji Invest. Participation from Intuit Ventures, Theory Ventures, General Catalyst, Contrary Capital, and Pathlight VC.

DOSS is trusted by fast-growing operators to run critical operations with speed, control, and confidence.

About the Role

The Forward Deployed Services team is Doss's core delivery engine. Every customer win runs through it.

This role sits at the intersection of product, professional services, and customer partnership. You'll own the end-to-end post-sales lifecycle for our largest clients while simultaneously building the capabilities and processes that scale the team as Doss moves upstream into upper mid-market and enterprise.

This is a player-coach role. You'll carry a book of strategic accounts while leading a team of PMO managers and building the function.

What You'll Do

Own the customer lifecycle. You're accountable for discovery, product design, build, UAT, and go-live across our most complex accounts. Success means clients achieve measurable value from Doss and become advocates.
Lead and develop the PMO team. You'll manage a team of PMO managers, set standards, drive calibration, and build a culture of ownership and accountability. You'll raise the floor and ceiling of the function.
Build new product capabilities. As Doss pushes into ENT, you'll identify gaps and build solutions within the platform. Part operator, part product thinker.
Set the standard for how the team works. You'll own best practices, process improvements, and tooling decisions across discovery, configuration, and go-live. If the team is doing something repetitive, you're thinking about how to automate or systematize it.
Partner cross-functionally. You'll work closely with Sales, Product, and Engineering, including our forward deploy engineers embedded in customer environments. Deep-dive into customer orgs to map workflows, translate them into product design, and collaborate on integrations and data migrations.
Drive AI-native operations. Doss is an AI-first company. You'll be expected to find and deploy AI and automation to improve delivery speed and quality across the team.

What We're Looking For

10+ years in professional services, consulting, operations, technical program management, or product operations at a technology company. ERP experience is a plus, not a prerequisite.
Experience managing and developing a team. You've built something before, not just contributed to it.
Familiarity with forward deploy or embedded engineering models, where technical resources operate directly in customer environments to drive adoption and accelerate time-to-value.
Systems thinker. Our business is highly interconnected across people, process, and technology. You see how it fits together and know how to untangle it.
High-intensity operator. You've thrived in high-pressure environments like startups, consulting, or finance.
Technical from first principles. You can work through hard engineering and logic problems from intuition. You don't need to be an engineer, but you can't be intimidated by one.
Strong analytical instincts. SQL is a plus. The ability to get to the right answer fast is required.
Customer obsession. You build real relationships with client stakeholders and treat their outcomes as your own.

What You'll Get