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Lead - Customer Growth
Freehand · San Francisco, United States
Pay
$95k–215k
Setting
On-site
About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
The Role & The Team
This role is that build. You will be the senior, advisory layer that sits above tactical implementation — the person who looks past the problem a customer hired us to solve, figures out what they're actually trying to achieve, and architects the path to get Freehand there. There is no playbook for this yet. You will write it, in partnership with a ~100-person team that has deliberately stayed lean, moves fast, and expects you to own outcomes end-to-end — not just flag them.
WHAT YOU'LL OWN
- Executive relationship & account strategy. Be the single-threaded owner of the post-go-live relationship for a portfolio of flagship F100 accounts (in the vein of Apple, Meta, J&J, Pfizer, P&G) — accountable for the outcomes they see.
- Land-to-expand strategy. Go beyond the category a customer bought us for (typically logistics AP) to map the full breadth of spend they're carrying — direct materials, warehousing & 3PL, services, MRO, trade & compliance — and build the case, with data, for where Freehand should expand next.
- Value realization & ROI storytelling. Translate agent performance — credits secured, cycle times cut, exceptions resolved autonomously — into a business narrative that resonates with CFOs, CPOs, and supply chain executives. Own renewal and expansion revenue for your accounts.
- Cross-functional influence. Sit close enough to product and engineering to shape what gets built next, and bring real customer signal back into the roadmap.
- Building the playbook. Because this remit doesn't fully exist yet, you'll spend real time defining it — what to measure, how to sequence expansion conversations, what "great" looks like 90 days after go-live versus 12 months in — and turning that into a repeatable model other future hires can run.
WHO YOU ARE
- First-principles problem solver. You've operated where the system doesn't exist yet — where you have to build the plane while flying it, and you're still accountable for the outcome. Consulting, banking, or operating roles inside ambiguous, high-stakes engagements are common paths here.
- Domain fluency. You've spent meaningful time in supply chain, logistics, procurement, or a comparably complex operating environment, and you can hold your own in a room with a customer's VP of Supply Chain or CFO.
- Energized by hard problems, with people. You do your best work pulling a room of smart, differently- skilled people toward a shared answer — you'd rather be one of several people solving something hard together than the sole owner of something easy.
- Honest about the edges of your own knowledge. You can say "I don't know, here's what I need from you to figure it out" to a client and mean it — and you're just as comfortable saying it internally.
- Builder, not just a manager. This is a senior, largely individual-contributor build role — in the mold of the director-level operators Freehand hires across every function — not a large-team management job. You'll be measured on outcomes you personally drive, not headcount you manage.
- Working at Freehand
Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :
- Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
- Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
- High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
- Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
- The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees Work Anywhere across the globe (we're remote & travel-first). We also cover your monthly home-internet costs. Every quarter, we arrange for a fully-paid trip to one of our Office Hubs to meet & interact with cross-functional teams.
In addition, we proudly offer the following Benefits to all our full-time employees:
- Take what you need Vacation Policy
- Full health coverage (with multiple gold-standard carriers across medical, dental & vision)
- Life Insurance and Disability benefits
- HSA/FSA Access
- 401(k) with a 4% Employer Match
- Fully-paid Parental Leave
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
Global Talent Partner
Freehand · San Francisco, United States
Pay
Not listed
Setting
On-site
About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
What You'll Do
- Own Freehand's talent strategy in the US end-to-end as the first dedicated US hire on the team — working directly with the CEO and Co-Founder(s) as a strategic partner, not just executing reqs
- Bring market intelligence to every search: research what talent realistically exists, and sharpen JDs and role definitions with hiring managers before sourcing begins
- Lead hiring across three priorities: building Freehand’s first SF-based engineering/product team, GTM roles (marketing, sales and pre-sales), and upgrading Professional Services/Deployment Strategists to serve Fortune 100 clients
- Build the US talent function from scratch — interview process, scorecards, tooling, and a clear definition of “what good looks like” for each role
- Own employer branding and Freehand’s EVP for a not-yet-known, technical brand, through audience-tailored storytelling, public presence, and community/event engagement
- Source creatively beyond LinkedIn — niche communities, events, alternative platforms, AI-assisted sourcing, and referral programs — to reach top 1–2% talent who aren’t actively looking
- Partner on retention and culture, feeding market intel back into Freehand’s people policies so the company stays a place top talent wants to join and stay
- Flex hiring pace to the business — senior/leadership searches are the core mandate, with the ability to scale to higher-velocity hiring pushes without lowering the bar
Who You Are
- Based in the SF Bay Area, comfortable with a hybrid setup
- 5+ years recruiting for new-age tech companies/startups, ideally including at least one 0-to-1 experience building a recruiting function from scratch; also open to ex-Sales candidates now running TA/recruiting for AI startups
- A recruiting background spanning both GTM and technical/engineering hiring — comfortable enough with technical detail to earn credibility with engineering hiring managers
- A demonstrated track record — not just a stated interest — in independently building employer brand, running or attending events, and finding creative ways to reach talent that isn’t easily found. Hunger and willingness to build matter more than polish here.
- Experience hiring for mid-to-senior and leadership-level roles as the core focus, not a junior or volume-recruiting background
- Thrives as a lean, senior IC: builds systems and process from scratch, and leverages AI tools and partners proactively in their work
- A true thought partner to leadership — comfortable having a seat at the table, not just executing what’s asked
Working at Freehand
Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :
- Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
- Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
- High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
- Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
- The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees Work Anywhere across the globe (we're remote & travel-first). We also cover your monthly home-internet costs. Every quarter, we arrange for a fully-paid trip to one of our Office Hubs to meet & interact with cross-functional teams.
In addition, we proudly offer the following Benefits to all our full-time employees:
- Take what you need Vacation Policy
- Full health coverage (with multiple gold-standard carriers across medical, dental & vision)
- Life Insurance and Disability benefits
- HSA/FSA Access
- 401(k) with a 4% Employer Match
- Fully-paid Parental Leave
Equal Opportunity
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
AI Deployment Strategist (San Francisco)
Freehand · San Francisco, United States
Pay
Not listed
Setting
On-site
About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
The Role & The Team
The AI Deployment Strategist role combines solution architecture, enterprise delivery, and strategic customer partnership. This role acts as the bridge between customers, product, engineering, and delivery teams to design, implement, and scale enterprise technology solutions. It requires both strategic thinking and execution capability, ensuring successful enterprise implementations while shaping product and solution direction.
WHAT YOU'LL DO
CUSTOMER PARTNERSHIP & STRATEGY
• Act as a strategic advisor to enterprise customers across operations, finance, supply chain, and IT teams.
• Partner with customers to define business objectives, requirements, priorities, and transformation roadmap.
• Build strong relationships with customer stakeholders from operational teams to executive leadership.
• Help customers rethink workflows, freight operations, payments, and enterprise processes through technology.
SOLUTION ARCHITECTURE & DESIGN
• Design end-to-end enterprise solutions integrating ERP, TMS, Spend management, and other enterprise systems.
• Create solution architecture, design documents, process flows, and implementation blueprints.
• Translate business requirements into scalable technical and functional solutions.
• Ensure solutions align with enterprise architecture, security, governance, and scalability requirements.
ENTERPRISE DELIVERY & IMPLEMENTATION
• Lead end-to-end implementation and migration of enterprise customers onto the platform.
• Drive execution across integrations, data migration, testing, and go-live.
• Manage complex, multi-stakeholder enterprise implementations.
• Ensure successful adoption, delivery excellence, and business value realization.
PRODUCT & ENGINEERING COLLABORATION
• Partner with product and engineering teams for integrations, feature adoption, and product improvements.
• Provide customer insights and feedback to influence product roadmap and platform capabilities.
• Act as the bridge between business stakeholders and technical teams.
BUSINESS ANALYSIS & PROCESS IMPROVEMENT
• Analyze customer data, workflows, and operations to identify improvement opportunities.
• Recommend process optimization, automation, and cost reduction opportunities.
• Define business outcomes and measure success metrics post-implementation.
DELIVERY EXCELLENCE & PLAYBOOKS
• Establish implementation best practices, frameworks, and delivery playbooks.
• Continuously improve delivery processes and implementation methodology.
• Help define and scale enterprise delivery organization standards.
Who You Are
• 6–15 years of experience in enterprise software implementation, solution architecture, consulting, or enterprise delivery roles.
• Experience in supply chain, logistics, freight audit payments, finance operations, or enterprise SaaS platforms preferred.
• Experience working with enterprise systems such as ERP, TMS, Spend management, or payment platforms.
• Proven track record of delivering complex enterprise implementations successfully.
• Bachelor's degree required; MBA or Operations/Supply Chain specialization preferred.
Working at Freehand
Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :
- Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
- Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
- High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
- Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
- The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees Work Anywhere across US & India (we're remote & travel-first). As and when required, for this role, we will also arrange for a fully-paid trip to our HQ in Chennai to meet & interact with cross-functional teams.
In addition, we proudly offer the following Benefits to all our full-time employees:
- Full Health coverage (accidental, life, vision, dental & health consultations)
- Monthly home-internet costs
- Flexible working hours
- Complimentary food & snacks at the Chennai HQ
Equal Opportunity
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
Strategic Partnerships
Freehand · United States
Pay
Not listed
Setting
Remote
About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
The Role & The Team
This is an individual contributor role, reporting directly into leadership, with no team to manage. We want someone who's genuinely hands-on: building their own decks, running their own demos, writing their own partner collateral, and closing their own relationships. There's no support infrastructure to lean on yet; you're building it.
We're open on exactly how this role is structured, depending on who we find:
- One person, both channels : If you bring real System Integrator (SI) and Private Equity/ISV partnership experience, we'll hire you into a single role covering both channels at a premium.
- Two people, one channel each: If your background is strong in only one of these areas, we're equally happy to hire two specialists.
- SI Partnerships: Could be a partner sales or partner marketing background — building and running relationships with systems integrators.
- PE Channel Partnerships: must have experience selling to industrial- or consumer-focused private equity firms, who in turn open doors to their portfolio companies.
- Alternative path: if the partnerships hires aren't a slam dunk, we're also open to a very hungry ABM marketer or product marketer with a track record of building strong external relationships and a genuine hustle to move into partnerships. Whichever shape this takes, you'll be one of the earliest strategic hires in this function, with outsized influence over how Freehand's partner ecosystem gets built from scratch.
What You'll Do
- Partner pipeline generation — Identify, prioritize, and build relationships with SIs, PE firms, and/or ISV/product partners relevant to accounts payable, procurement, supply chain, and finance ops
- Deal collaboration — Work hand-in-hand with these partners to source, co-sell, and close enterprise deals, acting as the connective tissue between their relationships and Freehand's sales motion
- Collateral and enablement, self-built — Create your own partner decks, one-pagers, demo scripts, and pitch materials; there's no dedicated support team, so you own the full production
- Demos and pitches — Run partner- and prospect-facing demos yourself, translating Freehand's agentic AI capabilities into value propositions relevant to each partner type
- PE portfolio company motion — For the PE channel, build the specific muscle of pitching PE firms on Freehand as a value-creation lever across their industrial/consumer portfolio, then working through to individual portco engagements
- SI relationship building — For the SI channel, build joint go-to-market motions, referral pipelines, and co-delivery relationships with systems integrators serving supply chain and finance transformation
- Feedback loop to product/GTM — Bring market and partner intelligence back to product and marketing to sharpen positioning and roadmap prioritization
Who You Are
- Startup or scale-up sales/partnerships experience — you've built something like this before, not just maintained an existing program
- High-pedigree intellect — top-tier engineering or MBA background
- An athlete or high performer in whatever form that's taken in your life — competitive, driven, and used to winning
- A true individual contributor at heart: scrappy, comfortable doing the work yourself (decks, demos, outreach) rather than delegating
- Some exposure to accounts payable, supply chain, finance, or logistics — you don't need to be a domain expert, but you should be conversant enough to build credibility fast
- If pursuing the premium single-role path: proven SI and PE/ISV partnership experience
- If pursuing a single-channel path: deep, specific experience in either SI partnerships or PE-channel selling (with the PE track specifically requiring experience selling to industrial/consumer-focused PE firms to reach their portfolio companies)
- If coming from marketing: a demonstrated hustle and relationship-building track record as an ABM or product marketer, with real hunger to move into a partnerships-facing role
- Comfortable with ambiguity and building process from scratch at an early-stage, fast-moving startup
Working at Freehand
Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :
- Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
- Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
- High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
- Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
- The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees Work Anywhere across US & India (we're remote & travel-first). As and when required, for this role, we will also arrange for a fully-paid trip to our HQ in Chennai to meet & interact with cross-functional teams.
In addition, we proudly offer the following Benefits to all our full-time employees:
- Full Health coverage (accidental, life, vision, dental & health consultations)
- Monthly home-internet costs
- Flexible working hours
- Complimentary food & snacks at the Chennai HQ
Equal Opportunity
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
Solutions / Technical Consultant
Freehand · United States
Pay
$50k–205k
Setting
Remote
ABOUT FREEHAND
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
THE ROLE & THE TEAM
We are hiring a Solution Consultant to lead technical solutioning and proof of concepts for strategic enterprise pursuits across North America. You will own the technical narrative end-to-end on named accounts — partnering with Account Executives on discovery, leading executive demos, building tailored collateral, structuring POCs, and serving as the customer-facing voice of the Freehand platform during the sales cycle.
Most pursuits will start with freight audit and pay as the wedge — it is where customers feel the pain first and where Freehand's value is fastest to prove. From there, you will help customers see the full picture: how the same decision platform extends across 3PL spend, logistics A/R, and global trade compliance to govern their broader supply chain spend.
This role sits at the intersection of Sales, Product, Delivery, and Engineering. You will work closely with AE leadership, the CTO and CPO offices, and the broader SC team. The work spans direct enterprise pursuits and advisory-firm-mediated deals (Kearney, PwC, and similar), where structured follow-up, executive-grade artifacts, and security and compliance fluency are non-negotiable.
WHAT YOU'LL DO
ENTERPRISE DEAL SOLUTIONING
• Own the technical pursuit strategy on named enterprise accounts from first technical conversation through signed contract
• Lead discovery sessions with stakeholders across logistics, finance, IT, and procurement to map current-state freight settlement processes and quantify pain
• Build and deliver tailored executive demos, technical deep-dives, and value engineering analyses that connect Freehand capabilities to customer-specific business outcomes
• Partner with Account Executives on deal strategy, stakeholder mapping, and competitive positioning
• Structure and lead POCs end-to-end owning milestone progression, engineering readiness, and customer-facing communication
SPEND DOMAIN EXPERTISE
• Serve as the customer-facing subject matter expert on enterprise freight audit and pay — invoice validation, contract and tariff matching, GL coding, accessorial review, exception handling, and payment execution
• Develop working fluency across Freehand's adjacent spend domains: 3PL and storage spend, logistics A/R, and global trade compliance (duties, HS classification, FTA eligibility, broker invoice validation)
• Position Freehand Pay as automated, reliable on-time execution of contractual payment terms — not early payment or factoring
• Articulate how Freehand integrates with customer ERPs, TMSs, WMSs, and banking infrastructure (EDI, API, SFTP)
AGENTIC PLATFORM SOLUTIONING
• Position Freehand as the decision layer for supply chain spend — translating the perception, context assembly, judgment, action, and accounting intelligence loop into language enterprise buyers understand
• Demonstrate the platform's agentic capabilities — Context Graph, agent directives, anomaly agents, Spend Intelligence, the AI Strategist persona, and agentic AP — to technical and executive audiences with credibility
• Show how Freehand's tiered feature rollout model delivers value across the customer journey
• Avoid overclaiming — calibrate framing to match what the platform actually does today versus what is on the roadmap
EXECUTIVE-GRADE COLLATERAL & COMMUNICATION
• Produce standing collateral — decks, one-pagers, technical briefs, security overviews — that can be reused across pursuits, not one-off responses to individual asks
• Maintain customer-facing artifacts including the Data Privacy & Security Overview and platform architecture documents in coordination with CTO and CPO offices
• Support advisory-firm-mediated deals (Kearney and similar) with the structured follow-up, technical depth, and polish those engagements require
• Contribute to RFP responses with accurate, current information on certifications (SOC 2, ISO 27001, ISO 27017/27018, ISO 42001, CSA STAR), platform capabilities, and deployment models
CROSS-FUNCTIONAL COLLABORATION
• Partner with Product and Engineering to surface customer feedback, validate roadmap priorities, and represent enterprise requirements in platform decisions
• Work with Implementation and Customer Success to ensure clean handoffs from sale to delivery and accurate scoping of committed capabilities
• Contribute to GTM enablement — training new AEs and SCs, building reusable demo environments, and developing playbooks for common deal patterns
• Coordinate with the broader SC team (US and Chennai Technical) on shared accounts, collateral standards, and POC execution
COMPETITIVE & INDUSTRY INTELLIGENCE
• Maintain working knowledge of the FA&P competitive landscape
• Track shifts in enterprise freight settlement, agentic AP, and BPO replacement trends that shape buyer expectations
• Translate competitive intelligence into positioning, battle cards, and objection handling for the broader GTM team
Who You Are
• 5+ years in supply chain or logistics technology, with 3+ years in a customer-facing pre-sales, solution consulting, or solution engineering role
• Demonstrated domain expertise in freight audit and pay or adjacent enterprise logistics finance workflows
• Experience leveraging AI in enterprise sales pursuits, paired with a genuine curiosity for using AI tools and methodologies to run discovery, build collateral, and advance deals more efficiently than traditional SC motions.
• Proven track record solutioning and closing enterprise SaaS deals with Fortune 1000 customers
• Strong written communication — able to produce executive-grade collateral independently, not reliant on marketing for every artifact
• Comfort engaging C-level and VP stakeholders across logistics, finance, and IT
• Working fluency in enterprise security and compliance posture (SOC 2, ISO 27001, ISO 27017/27018, ISO 42001, CSA STAR, data privacy frameworks) and ability to discuss credibly with customer security teams
• Familiarity with enterprise SaaS integrations (ERP, TMS, EDI, API, SFTP)
• Willingness to travel across North America for customer meetings, workshops, and industry events (estimated 25-40%)
WORKING AT FREEHAND
We proudly offer the following Benefits to all our full-time employees:
- Take what you need Vacation Policy
- Monthly home-internet costs
- Full health coverage (with multiple gold-standard carriers across medical, dental & vision)
- Life Insurance and Disability benefits
- HSA/FSA Access
- 401(k) with a 4% Employer Match
EQUAL OPPORTUNITY
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
Chief of Staff / Strategic Finance
Freehand · San Francisco, United States
Pay
$115k–210k
Setting
On-site
About Freehand
Freehand (freehand.ai http://freehand.ai) is building autonomous AI agents for enterprise spend management, replacing internal and outsourced (BPO) headcount and shared service centres with "AI Employees" across procure-to-pay and order-to-cash workflows, selling to Global 2000 CFOs.
Freehand counts Apple, Meta, J&J, Pfizer, Cardinal Health, Dunkin', and Samsara among its customers. We're now scaling the team across GTM, product, and operations.
The Role
We're hiring two Founder's Office roles to take on the highest-leverage strategic projects across the company: fundraising, board and investor comms, org design, key customer expansions, revenue operations, cost optimization, and special initiatives that don't yet have an owner. You'll work directly with the CEO and leadership team, with end-to-end ownership of workstreams that shape how Freehand scales. This is a front-row seat to building a category-defining enterprise AI company in San Francisco.
How we think about the business
Freehand, like any business, runs on five pipelines: capital, talent, sales, implementations, and product. Each has its own throughput, conversion, and cycle time, and each both constrains and feeds the others, and the overall business. The Chief of Staff / Strategic Finance role is to make those interactions legible, financially, operationally, and visually, and to actively de-bottleneck them.
What you'll do
- Build the top-down financial model of the business as the intersecting output of the five pipelines, and decompose it into functional models for sales, implementations, product, talent, and capital
- Identify the dynamic binding constraint in each pipeline and at the company level; quantify the cost of each bottleneck and the ROI of unblocking it
- Stand up dashboards for each pipeline and a consolidated business view, leading indicators, throughput, conversion, cycle time, unit economics
- Partner with each function head to set weekly, monthly and quarterly goals tied to the model, and drive a prioritized list of debottlenecking initiatives across the company
- Run weekly functional reviews and fortnightly business reviews alongside the CEO
- Own strategic initiatives across customer expansion, pricing, org design, and cost optimization, and other high-leverage problems that don't yet have an owner
- Run board meetings end-to-end: materials, narrative, follow-ups, investor materials, modeling, process management
Ideal background
- CS undergrad from top tier college in India (IIT/NIT) or the US (Ivy League school); MBA from HBS, Wharton, or Stanford
- At least 2-4 years in investment banking or private equity
- At least 2-4 years in an operating role (BizOps / Strategic Finance) at a consumer tech or B2B software company
- Founder or very early-stage startup experience is a strong plus
- Proven track record of hands on financial modelling across GTM, product, tech and ops; comfortable moving between board-level strategy, management decision making and hands-on functional execution
Working at Freehand
We proudly offer the following Benefits to all our full-time employees:
- Take what you need Vacation Policy
- Monthly home-internet costs
- Full health coverage (with multiple gold-standard carriers across medical, dental & vision)
- Life Insurance and Disability benefits
- HSA/FSA Access
- 401(k) with a 4% Employer Match
Equal Opportunity
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
GTM Architect
Freehand · United States
Pay
$120k–240k
Setting
Remote
About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
The Role & The Team
As our first GTM Architect (aka Sales / Revenue Enablement) hire, you'll build the function from scratch — the playbook, the collateral, the training, the systems. You'll work shoulder-to-shoulder with our Founder CEO, CRO and sellers to understand what's winning, then turn that into infrastructure that scales. This is a commercial role - we want someone who thinks like a seller, uses AI as a reflex, and has opinions on where our next market segment is.
What you'll own:
- Seller onboarding, training programs, and certification frameworks
- Sales collateral including decks, one-pagers, battle cards, objection guides
- GTM narratives for new segments, verticals, and use cases
- Enablement tooling and content systems, built with AI where it removes friction
- Leading indicators that tie enablement activity to pipeline and revenue
Who You Are
3–5 years in field/ revenue/ sales enablement, ideally at an early-stage B2B AI or SaaS company. You've built from a blank page before and you're energized by it.
- Designed, own and run seller training programs end-to-end
- Built collateral field teams actually use — you know why most decks fall short
- Written GTM narratives: ICP, value prop, competitive positioning, the pitch itself
- Native AI user — it's in how you draft, research, build, and find leverage
- Thinks at the market level: spots adjacencies, new segments, brings ideas forward
- Has genuine credibility with sellers, earned from time working alongside them
Working at Freehand
Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on :
- Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
- Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
- High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
- Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
- The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees Work Anywhere across the globe (we're remote & travel-first). We also cover your monthly home-internet costs. Every quarter, we arrange for a fully-paid trip to one of our Office Hubs to meet & interact with cross-functional teams.
In addition, we proudly offer the following Benefits to all our full-time employees:
- Take what you need Vacation Policy
- Full health coverage (with multiple gold-standard carriers across medical, dental & vision)
- Life Insurance and Disability benefits
- HSA/FSA Access
- 401(k) with a 4% Employer Match
- Fully-paid Parental Leave
Equal Opportunity
Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.
Listed by Freehand for a position based in the United States. Employers on this board attest they are hiring domestically.
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