Commercial Cofounder — Head of Sales & Marketing

Commercial Cofounder — Head of Sales & Marketing

Location: Remote

Commitment: Full-time, or a short agreed transition to full-time

Compensation: 20% founder equity; no cash salary currently

Company: Tocayo Labs

Stage: Live product, early revenue, pre–product-market fit

About Tocayo

Tocayo helps local business owners create and manage their online presence without becoming website designers.

A business owner answers a few questions and Tocayo generates a complete, hosted website. They can refine it conversationally, publish it, connect a domain, receive customer inquiries, manage bookings, and understand how their site is performing.

This is not an idea-stage project or an unfinished prototype. Tocayo is live, has generated more than 130 business websites, and supports free and paid customers. You can see the product and customer examples at tocayo.me.

The product is substantially further along than the commercial engine. We have early customers, working acquisition and analytics infrastructure, and real sites to demonstrate, but we have not established a predictable way to acquire and retain paying customers. Distribution, positioning, conversion, and customer learning are now company-defining problems.

We are looking for a commercial cofounder who wants to own those problems directly—not someone who wants to manage an agency, supervise a future sales team, or create a marketing plan for somebody else to execute.

The opportunity

Tocayo was built by a solo technical founder. The company now needs a second founder whose primary craft is creating demand, selling, learning from customers, and turning those lessons into a repeatable go-to-market system.

You will join as a genuine cofounder with meaningful ownership and company-level decision-making authority. You will work alongside the technical founder to decide whom Tocayo should serve, how we should reach them, which promises resonate, where prospects lose confidence, what should change in the product, and which channels deserve investment.

This is an intensely hands-on role. At the beginning, you will make the calls, answer inbound leads, run demos, follow up, close customers, write the copy, create the videos, publish the content, test campaigns, and maintain the pipeline yourself.

The goal is not to make Tocayo look busy. The goal is to find a repeatable path from a clearly defined customer problem to activated, retained, paying customers.

What you will own

• Share company-level strategy, positioning, pricing, product, and go-to-market decisions with the technical founder.
• Define and continuously refine Tocayo's ideal customer profile using sales evidence rather than broad market labels.
• Personally conduct high-volume, high-quality outbound prospecting, including cold calls, follow-up calls, email, direct messages, and other appropriate channels.
• Own inbound sales from first response through qualification, demonstration, objection handling, follow-up, close, onboarding, and early retention.
• Build a disciplined sales pipeline with clear stages, next actions, conversion rates, loss reasons, and revenue attribution.
• Develop and test sales scripts, offers, messaging, landing-page copy, demonstrations, and follow-up sequences.
• Produce launch videos, product demonstrations, founder-led videos, customer stories, and short-form social content from concept through publication.
• Build a sustainable content system that repurposes customer questions, objections, demonstrations, and product outcomes across relevant channels.
• Select social platforms based on customer evidence and channel performance rather than trying to maintain a presence everywhere.
• Design and run bounded growth experiments across outbound sales, content, referrals, partnerships, communities, local organizations, lifecycle marketing, SEO, events, and paid acquisition when the economics justify it.
• Turn sales calls, lost deals, activation problems, and retention signals into specific product and positioning recommendations.
• Work with the technical founder to improve the path from landing page to onboarding, published website, paid conversion, and retained use.
• Develop permissioned customer proof, including testimonials, case studies, before-and-after demonstrations, and measurable outcomes without inventing or overstating results.
• Establish weekly commercial reporting focused on qualified pipeline, sales activity, activation, paid conversion, retention, acquisition cost, and revenue—not followers or impressions in isolation.
• Build the sales and marketing playbook that future hires can follow, then help recruit and lead those hires when the company can support them.
• Participate in fundraising, partnerships, strategic planning, and other founder responsibilities.

What already exists

You will not be starting with a pitch deck and a hypothetical product. Tocayo already has:

• A live product with real generated business websites and customer examples.
• A free entry point, paid subscription, and optional hands-on onboarding offer.
• A self-serve onboarding flow that can take a business from basic information to a live website.
• Website editing, publishing, domains, lead capture, booking, analytics, and search-readiness features.
• Instrumentation across landing-page visits, onboarding, account creation, project creation, checkout, and subscription outcomes.
• Lifecycle and draft-recovery email capabilities.
• Search content, technical SEO foundations, and an operating framework for organic growth.
• Existing social, video, advertising, and customer-outreach assets that can be evaluated, reused, or discarded.

These are starting assets, not proof of a working growth engine. You will be expected to determine what actually creates customers and eliminate activity that does not.

What we are looking for

You are likely a strong fit if you:

• Have personally sold a product or service through cold calling and can demonstrate the activity, conversations, meetings, and revenue that resulted.
• Know how to handle inbound leads quickly, qualify them, run a useful demonstration, follow up consistently, and ask for the sale.
• Have built an early sales motion before a mature brand, large budget, sales-development team, or extensive marketing automation existed.
• Can move between strategic positioning and direct execution in the same day.
• Can write clear, persuasive copy without hiding behind jargon, inflated claims, or generic AI language.
• Can create effective launch and demonstration videos, including concept development, scripting, recording or screen capture, editing, captions, distribution, and repurposing.
• Have produced social content that generated qualified conversations, signups, pipeline, partnerships, or revenue—not merely views.
• Understand how to test offers, audiences, messages, and channels with explicit hypotheses and measurable outcomes.
• Are comfortable speaking directly with local business owners and adapting to people who may not use technical or startup language.
• Can hear repeated objections without becoming defensive and translate them into better positioning, product decisions, or qualification criteria.
• Understand the difference between acquisition, activation, conversion, retention, and referral.
• Can operate with incomplete data while refusing to manufacture certainty from small samples.
• Maintain an accurate CRM and follow-up discipline even when the process is still founder-led and manual.
• Are willing to stop campaigns and channels that produce attention without customers.
• Want the responsibility and ambiguity of founding a company, not merely an executive title.

Strong candidates may come from startup sales, founder-led sales, agency growth, local-business services, demand generation, product marketing, or content-led acquisition. Evidence of personally creating revenue matters more than a particular previous title.

Particularly relevant experience

Any of the following would be valuable but is not required:

• Selling SaaS or services to local and owner-operated businesses.
• Cold calling contractors, home-service businesses, professional services, wellness businesses, or other small-business segments.
• Founder-led sales at a pre-seed or pre–product-market-fit company.
• Selling products with free-to-paid conversion or product-led onboarding.
• Creating product-launch campaigns and short-form demonstration videos.
• Building an audience through useful, founder-led content.
• Running customer interviews, win/loss analysis, pricing tests, or offer design.
• Lifecycle email, CRM operations, lead scoring, or sales automation.
• Local partnerships, chambers of commerce, trade associations, referral programs, or channel sales.
• Organic search, digital PR, community distribution, paid social, or retargeting.
• Marketing analytics, funnel analysis, attribution, and experiment design.
• Recruiting or leading an early sales and marketing team after personally proving the motion.

What success looks like in the first 30 days

• Learn the product by creating, editing, publishing, and selling a Tocayo website yourself.
• Review existing customer evidence, pricing, positioning, acquisition attempts, funnel data, content, and outreach assets.
• Speak with current users, paying customers, lost prospects, and relevant business owners.
• Propose an initial ideal-customer profile and the evidence that would confirm or disprove it.
• Establish a simple, accurate CRM and pipeline baseline.
• Begin personally handling inbound leads and conducting daily outbound activity.
• Produce an initial sales narrative, call script, objection library, demonstration flow, and follow-up sequence.
• Ship the first new proof-driven demonstration or launch video.

What success looks like in the first 90 days

• Maintain a consistent cadence of qualified customer conversations, demonstrations, follow-ups, and closes.
• Identify which customer segment, problem, promise, and offer generate the strongest sales response.
• Run a small number of clearly measured acquisition experiments rather than many disconnected campaigns.
• Establish reliable reporting from lead source through activation and paid conversion.
• Build a repeatable process for turning sales evidence into landing-page, onboarding, pricing, and product changes.
• Publish a consistent stream of useful demonstrations, customer education, founder content, and permissioned proof.
• Document why prospects buy, why they decline, why users fail to activate, and why customers remain or leave.
• Produce an evidence-based recommendation about which channels should be scaled, changed, or stopped.

What success looks like in the first six months

• Establish a defensible initial ideal-customer profile and positioning wedge.
• Create a sales process another capable person could follow and improve.
• Demonstrate a repeatable path to acquiring and activating paying customers, even if it is still founder-led and not yet scalable.
• Improve at least one company-level commercial outcome such as qualified pipeline, sales conversion, activation, paid conversion, retention, or referral.
• Build a credible library of demonstrations, customer proof, objection handling, and sales enablement material.
• Produce a grounded growth plan tied to actual conversion economics rather than aspirational audience size.
• Define when the company should add sales, customer-success, content, or performance-marketing hires.

Cofounder terms

This position offers 20% founder equity and currently offers no cash salary.

The final grant will be documented through definitive company agreements, including the capitalization basis, vesting, intellectual-property assignment, governance rights, and treatment of future financing. The expected structure is long-term founder vesting, with the precise commencement date and cliff agreed before work begins.

There is no guaranteed date on which salary will begin. Adding founder salaries will depend on revenue, financing, runway, and mutual approval. Any candidate should assume that the equity is illiquid, may be diluted by future financing, and may ultimately be worth nothing.

This is not a commission-only sales position disguised with a founder title. The ownership is substantial because the commercial mandate, risk, authority, and company-level responsibility are substantial.

This is probably not for you if

• You require cash compensation immediately.
• You want to manage an existing sales team rather than personally sell.
• You are unwilling to cold call or follow up repeatedly.
• Your experience is primarily brand strategy without direct revenue accountability.
• You need a large advertising budget, agency, production team, or established audience before you can make progress.
• You measure marketing success primarily through impressions, followers, engagement, or content volume.
• You want to outsource content creation before proving the message yourself.
• You expect the technical founder to generate your lead lists, write your scripts, operate the CRM, or close your deals.
• You use aggressive claims, fabricated urgency, purchased engagement, spam, or misleading customer proof.
• You are looking for a short-term consulting or freelance engagement.
• You cannot make a serious path toward full-time commitment.
• You are uncomfortable having your assumptions challenged by customer behavior and measured outcomes.

How to apply

Please include:

• A brief explanation of why a commercial cofounder role makes sense for you now.
• A specific cold-calling example: what you sold, whom you called, your role, approximate activity, conversion, and revenue outcome.
• An inbound-sales example showing how you qualified, demonstrated, followed up with, and closed prospects.
• One launch, product-demonstration, or sales video you personally helped create, with a clear description of your contribution.
• Examples of social or marketing content that generated qualified conversations, pipeline, partnerships, signups, or revenue.
• A low-budget growth experiment you personally designed and executed, including what worked, what failed, and what you changed.
• Your current location, availability, and expected path to full-time commitment.
• The questions you would need answered before accepting 20% equity with no current salary.

Please do not send a generic cover letter or a list of marketing channels. We are interested in what you personally sold, created, measured, learned, and changed.