POWERING THE WORLD'S LEADING DTC BRANDS
— JOIN THE FOUNDING TEAM
Help us design the future of every brand.
Olivia is the world's first agentic DTC AI design platform — purpose-trained on 10,000+ of the highest-revenue, highest-converting brands on the planet, updated constantly. Built by DTC operators and AI engineers whose combined decade of brand and agency relationships becomes our first customer base. The team that joins today will be the people who shaped it.
Performance incentive compensation
Vested equity in Olivia AI
Growth & milestone bonuses
AI & agentic workflows — 8–10x your output
Remote-first · Annual retreat
OUR MISSION
We're building toward 1,000,000 DTC brands globally using Olivia every single day — for every ad, email, product photo, and landing page they need to grow. The same way OpenAI brought AI to nearly every person on the planet, Olivia will bring agentic generative design to nearly every business in the world.
BACKED BY THE WORLD'S LEADING TECHNOLOGY PROGRAMS
— THE MOMENT
Why now is the only time that matters
The $6.3 trillion eCommerce industry is facing its most critical bottleneck at the exact moment generative AI crosses its commercial viability threshold. Brands don't just need more creative — they need high-converting, ever-evolving creative that adapts as the landscape changes. Consumer attention shifts. Platforms change their algorithms. What converted last quarter won't convert next quarter.
Olivia is purpose-trained on 10,000+ of the highest-revenue, highest-converting DTC brands — updated constantly so the model evolves with the market. Generic AI tools weren't built for this. ChatGPT, Midjourney, and Adobe Firefly generate images. They don't generate production-ready agentic creative that knows your brand, your category, and what converts.
This is a unique crossection of DTC expertise and AI engineering that almost no team on the planet has. With 10+ years of brand and agency relationships ready to become customers, the first-mover window to define the category of agentic generative design is open right now — and closing fast.
$6.3T
Global eCommerce market running on design and creative every day
$178B
DTC design & creative industry Olivia is fundamentally reshaping
10K+
Top brands Olivia is trained on — highest revenue and conversion, updated constantly
10x
More high-converting creative brands need — Olivia delivers it, evolving with the market
We're not looking for motivated. We're looking for hungry.
Olivia is the best thing we've ever built — and we know what it can become. We need people who feel that in their gut. A deep, driving desire to build something truly remarkable — not because it's a good career move, but because the opportunity to define an entirely new category of agentic AI design doesn't come around twice. If you've been waiting for the right thing to pour yourself into, this is it.
We know exactly who this isn't for.
We're not being harsh. We're being honest — because the right people will read this and feel relieved, not warned off. The people who thrive here already know they belong. And the people who don't will save us both time by knowing that now.
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People who need a playbook before they can move. We don't have one. You'll build it.
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People who "manage" channels from a distance. We need owners who are in it close range, daily.
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People whose AI use starts and ends with prompting ChatGPT. We need architects, not users.
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People who separate strategy from execution. Everyone here does both. That's not a phase — it's the culture.
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People who need consensus before they act. We move fast. Deliberate and decisive, not slow and safe.
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People whose best work required a big team and a big budget. We're lean by design and that's a superpower.
One million brands. One platform. One team to build it all.
Every founder who ever struggled to afford a designer. Every brand team that waited six weeks for a photoshoot. Every agency that turned away clients because they ran out of bandwidth. Olivia exists for all of them. And the team we're building right now is the team that makes that real — not someday, but in the next 18 months. The window to be that team is open. It won't be open for long.
— HOW WE WORK
Agentic by design — every role, every day
Adapt · Don't just adopt
You don't just use AI. You orchestrate it.
Every role at Olivia comes with a personal team of AI and agentic workflows — agents you build, manage, and continuously improve. Outreach agents, research agents, content repurposing agents, pipeline intelligence, churn signal detection. Tools that operate at a scale no individual could reach manually.
We look for people who have experience producing real results with AI and agentic tools in a previous role. And we want people willing to adapt, not just adopt — don't copy what everyone else is doing. Build the workflow that works for your role at Olivia and improve it every week.
If you've never worked with agents, we'll invest in getting you there. If you already run your own agent stack, we built this company for people like you.
AGENTIC SALES
Outbound research agents, personalization at scale, follow-up sequence automation, pipeline intelligence — your CRM works while you sleep. Generative creative via Olivia for every sales asset.
AGENTIC CONTENT
Repurposing agents, Olivia for all generative creative, scheduling automation — one podcast episode becomes 20 assets across every platform automatically.
AGENTIC GROWTH & RETENTION
Health scoring agents, churn signal detection, expansion opportunity ID, funnel analytics — the full board visible and actionable in real time.
AGENTIC PERFORMANCE
All ad creative generated by Olivia, A/B test analysis agents, attribution modeling — your paid stack runs smarter and proves the product works simultaneously.
— WHAT WE STAND FOR
Core values
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We hire people who think like owners. You see the gap, make the call, and move. Every role carries real accountability and real authority to act without being told to.
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We operate on real numbers and honest claims we can defend. "90% accuracy" not "the best AI ever." This is how we earn lasting trust with the brands we serve.
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We move fast because the market is moving fast. We bias toward action and iterate. Done and learning beats perfect and late, every time.
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You'll wear multiple hats — that's not a warning, it's a feature. Mastery within your core role is non-negotiable. Genuine contribution beyond it is expected. Outcomes over job descriptions.
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No hidden agendas, no politics. We share what's working and what isn't — with each other and with the brands we serve. Honesty builds the kind of trust that compounds.
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Every dollar freed up goes back into growth. We eat our own cooking — Olivia runs all of our own generative creative. If we wouldn't use it ourselves, we don't ship it.
— WHO YOU'LL WORK WITH
Olivia was born from a decade of personal experience in the trenches of DTC. Benson spent years scaling brands from zero to $50M+, then founded D2C Design — a design agency built specifically to serve the top 10% of DTC brands in North America. It was working inside that world, billing for every asset, watching brands wait weeks for creative they needed yesterday, that made the problem undeniable. Jacob brings the AI-native engineering to make the solution real — proprietary generative and agentic systems built from the ground up. This is not a market gap identified from the outside. It's a problem we lived, and we built Olivia to permanently fix it.
B
Benson Sung
Co-Founder & CEO
Scaled DTC brands to $50M+. Founded D2C Design, serving North America's top 10% of DTC brands. Built Olivia from the inside out.
J
Jacob Ferrari
Co-Founder & CTO
AI-native engineer. Deep systems and prompt engineering expertise. Building Olivia's proprietary generative and agentic infrastructure.
N
Nabeel
Head of Product & Brand
Product design and brand direction. Shaping how Olivia looks, feels, and works for every brand that uses it.
J
James S.
Growth & Customer Ops
Pipeline, onboarding, and retention. Keeping the early engine running while the growth team is assembled.
— WHAT YOU GET
Benefits & compensation
📈
Performance comp
Base plus meaningful performance incentives tied directly to your KPIs. Scales as Olivia scales.
🌿
Vested equity
Real ownership in Olivia AI. When we win, you win in the way that actually matters.
⚡
Growth bonuses
Milestone and company growth bonuses tied to real outcomes — not symbolic gestures.
🌍
Remote-first
Work from wherever you do your best work. We're building a global product for global brands.
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Annual retreat
One annual team retreat — Tokyo, Taiwan, or Canada. A week to build, align, and push the vision forward together.
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R&D budget
Dedicated budget for tools, AI experiments, and anything that makes you more effective at your craft.
🎯
Founder access
Direct access to Benson and Jacob. No layers, no politics. Your ideas reach the decision room same day.
— OPEN ROLES
Where you fit in
01 / 06
Head of Brand Sales & GTM
The person who takes Olivia from invite-only to the agentic design platform every DTC brand team knows by name.
THE ROLE
You own the entire brand-side revenue motion. Not just closing deals — building the machine that makes pipeline predictable. The demo-to-paid close rate is already exceptional; your job is volume, velocity, and systematizing the motion across every DTC vertical: beauty, apparel, supplements, beverage, home goods, pet, wellness.
WHAT YOU OWN
Full demo-to-paid sales motion for DTC brand teams
Webinar program — weekly live demos driving pipeline
Events — Olivia's presence at Shopify, Klaviyo, DTC conferences
Referral & affiliate program for the brand channel
Sales reporting and pipeline visibility
Product feedback loop from live sales conversations
AGENTIC STACK
Outbound research
Personalization agents
Follow-up automation
Pipeline intelligence
KPIS
Primary: Topline brand MRR
Flow: Demos booked per month
Conversion: Demo-to-close rate
Expansion: Referral pipeline
02 / 06
Head of Agency & Partnerships
The architect of Olivia's distribution engine — where one conversation becomes fifty brand accounts using generative AI design.
THE ROLE
Agencies are Olivia's highest-leverage distribution channel. One partnership means 10–50 brands onboarded through a single relationship. This is a relationship-building role that compounds — you acquire the right agencies across all seven DTC types, activate them fully, and build the tech partnerships with Shopify, Klaviyo, and the platforms the DTC ecosystem runs on.
WHAT YOU OWN
Agency acquisition across all seven DTC agency types
Full agency lifecycle from signed to revenue-generating
Strategic partnerships with Shopify, Klaviyo & tech platforms
DTC mastermind and community relationships
Partnership referral pipeline tracking & activation
Agency training, playbooks & enablement
AGENTIC STACK
Agency research agents
Relationship CRM
Partnership tracking
Activation scoring
KPIS
Primary: Topline agency MRR
Partners: Agencies onboarded per quarter
Distribution: Brands through agency channel
Referrals: Partnership referrals
03 / 06
Head of Content & Community
The person who makes Olivia famous in DTC before a brand has ever seen a pitch deck — using agentic content workflows to move at a scale most teams can't match.
THE ROLE
You own the organic top-of-funnel and every social touchpoint Olivia has in the world. The podcast is the content anchor — live brand teardowns, live generative design sessions, cost reveals, founder interviews. Clips become the acquisition engine across LinkedIn, TikTok, and Instagram. You build your own platform as part of the role. Your audience becomes ours.
WHAT YOU OWN
Podcast — production, editorial, guests & distribution
Clip strategy — 10–20 assets per episode per platform
All social channels — LinkedIn, TikTok, Instagram, YouTube
Influencer program across all social channels
UGC — before/afters, speed demos, generative design reveals
In-person events in partnership with agencies
Personal brand building as part of the role
AGENTIC STACK
Content repurposing agents
Scheduling automation
Olivia for all creative
SEO content agents
KPIS
Primary: Organic demo bookings
Reach: Follower growth & clip reach
Media: Podcast downloads
Influence: Influencer impressions & referral traffic
04 / 06
Head of Performance
The engine room — turning proven organic content and generative creative into paid pipeline at scale, using Olivia to produce every ad you run.
THE ROLE
You join after the organic engine is proven and pour fuel on what's working. Drive demo bookings through paid acquisition at scale using Olivia itself to produce every ad creative. Every campaign is simultaneously a revenue play and a live demonstration of Olivia's generative design capabilities. You use the same agentic AI your customers use.
WHAT YOU OWN
Paid acquisition — Meta, TikTok, LinkedIn & Google
Landing page and funnel conversion optimization
Content amplification — organic clips into paid placements
All ad creative generated via Olivia
CAC and LTV optimization by channel
Retargeting and unconverted lead nurture
Attribution and paid performance reporting
AGENTIC STACK
Olivia for all creative
Bidding optimization
A/B test analysis
Attribution modeling
KPIS
Primary: Paid-attributed MRR
Efficiency: Cost per demo booking
Channel: ROAS by platform
Funnel: Traffic & lead flow to pipeline
05 / 06
Head of Growth
The person who sees the whole board — and makes every channel, every agent, and every team member compound toward one million brands.
THE ROLE
You own the full-funnel architecture that makes the entire revenue engine work as one system. Outbound and inbound systems, growth modeling, CRM infrastructure, experiment roadmap — you connect Brand Sales, Agency, Content, and Performance into a coherent machine and give Benson a clean, accurate forward view of what's coming.
WHAT YOU OWN
Outbound and inbound systems infrastructure
Full-funnel architecture and conversion optimization
Growth modeling and revenue forecasting
CRM, pipeline tracking & attribution
Structured experiment roadmap across all channels
Cross-team weekly growth coordination
New channel identification & evaluation
Product-to-marketing feedback synthesis
AGENTIC STACK
Outbound sequence agents
Lead scoring agents
Pipeline forecasting
CRM automation
KPIS
Primary: Total MRR growth
Acquisition: CAC by channel
Funnel: Lead-to-demo & demo-to-close rates
Velocity: Funnel efficiency across all stages
06 / 06
Head of Retention
The protector of every dollar earned — turning brands that discovered agentic generative design into long-term partners who bring their entire network.
THE ROLE
Acquisition gets brands in the door. You make sure they never leave — and that they expand, refer, and become Olivia's loudest advocates. Fast activation, expansion MRR, churn prevention, referral program management, and the case study engine that gives the sales team its most powerful proof assets. You own the LTV side of the equation.
WHAT YOU OWN
Customer onboarding and first-value activation
Ongoing customer success & relationship management
Expansion MRR — upsells, cross-sells, plan upgrades
Churn prevention and at-risk account intervention
Referral program design & management
Case study and testimonial content pipeline
Product feedback synthesis for the founding team
Enterprise and agency renewal management
AGENTIC STACK
Health scoring agents
Churn signal detection
Expansion opportunity ID
Renewal agents
KPIS
Primary: Net revenue retention
Retention: Logo retention rate
Expansion: Expansion MRR month-over-month
Velocity: Time-to-first-value
QUESTIONS
What people ask before they apply
Do I need a background specifically in DTC or eCommerce?
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What AI and agentic experience do you actually expect?
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What does wearing multiple hats actually mean here?
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Is the equity real — what does vesting look like?
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Are these roles fully remote?
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What stage is Olivia at right now?
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How is compensation structured?
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How quickly can I grow into a broader leadership position?
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What does the interview process look like?
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Why is right now the right time to join Olivia?
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We hire for outliers, not resumes.
Small team. Real ownership. Your comp scales with the revenue and partnerships you drive. Equity vests as we grow. We're building toward one million brands — using agentic generative design, every day, for every piece of creative they need. We need the people who want to be the reason it happens.