Head of Marketing "Rainmaker"

Link to apply listed at the bottom of this Job Description. Only applications submitted through this link will be considered.

WHO WE ARE

Spyglass Ops helps founders scale themselves and their visions through operations. We partner with 7-8 figure digital entrepreneurs who are scaling with purpose: leaders who value impact, and a people-first approach to growth.

Our mission is to transform operations from a bottleneck into the highest leverage point for business impact, growth, profit & freedom. We don't do cookie-cutter solutions. We dive deep to understand our client’s businesses, goals, and them as a person, then we level up their team & Ops foundation so they can scale toward their version of business and life that matters most.

Founded by Jhana Li almost 5 years ago, after serving as COO at two successful startups, Spyglass has evolved from operator coaching to full-service, high-ticket operations transformation, including Fractional COO consulting, "done for you" operations recruitment, and Operations + leadership coaching.

Our Core Values are:

• Play Like A Nerd: We are a team of nerds, each hopelessly passionate and excited about our area of expertise. We believe that if you are an absolute nerd for what you do, then work is play. And we play hard.
• Own Your Opportunities: Every mistake and failure is an opportunity. See it and use it as such. Take as much ownership as you possibly can, and use it as feedback to improve. The only two words you'll never hear at this company: fault and blame.
• Commit to Your Own Potential: We expect this of ourselves, each other, and our clients: to relentlessly, critically be redefining and growing into the most potent version of ourselves and the impact we can have.
• Van Talk: Discovered while Jhana was traveling full-time in a van through South America, Van Talk is not just a willingness and ability to speak honestly. It is a way of receiving crucial communication, not as a personal affront, but as a genuine and necessary act of service to accomplish our shared goals and highest potential.

If our culture and mission does not resonate with you, please do not bother applying.

JOB DESCRIPTION

The Spyglass Ops team is seeking a strategic, experienced marketing leader who will serve as our "Rainmaker," the person who owns all marketing outcomes and drives revenue growth from $1.2M to $4M+ over the next two years.

This is our first full-time marketing hire, which means you'll have the rare opportunity to architect and own the entire marketing function from the ground up. You'll be supported by fractional team members (including our founder for brand building and content, our operations team for data systems, and current agency partners), but the strategic vision and execution accountability sits squarely with you.

What makes this role unique: Our founder, Jhana Li, is a powerful personal brand asset who will continue creating front-facing content and thought leadership. Your job is NOT to replace her presence. It's to strategically leverage her brand to drive short-term results while simultaneously building an evergreen, founder-independent marketing machine for long-term scalability. The application code word is LEVERAGE.

You will maximize our current working channels (referrals and events, which are strong but have room for optimization), accelerate our emerging channels (YouTube and email, which are showing promising early traction), and develop entirely new revenue streams (including breaking into the startup M&A market).

This role requires someone who has done this before. We are hiring on proven track record, not potential. You should be able to walk in on day one and know exactly what great marketing looks like at this stage of growth, because you've built it yourself multiple times.

This is a remote, full-time 1099 contractor position with complete autonomy over your schedule and execution. Given the critical nature of this role, we host a rigorous, multi-part application process to ensure the right fit.

WHAT MAKES THIS ROLE UNIQUE

You're stepping into a company at an inflection point. We've proven our business model, we have strong founder-driven traction, an exceptional product, and the backend systems and team capable of 3-4X growth. Our key strategic bottleneck is marketing, that’s where you come in.

Your success will be measured by one ultimate outcome: building a dual-growth engine that maximizes Jhana's personal brand impact in the near term while creating founder-independent marketing systems that drive long-term, sustainable revenue.

You'll work directly with Jhana on strategy and brand leverage, but you'll own all marketing decisions, initiatives, and outcomes. This role requires someone who understands that a powerful founder brand is an asset to be strategically deployed, not a crutch on which to create dependency.

Within your first 30 days, you'll produce a robust 12-month marketing game plan. Within 60 days, you'll be implementing initial action steps. Within 90 days, we expect to see strong leading indicators and first leads coming through from your marketing efforts.

RESPONSIBILITIES (TASKS ASSOCIATED WITH THE ROLE)Strategic Marketing Leadership

• Own all marketing strategy and initiatives from conception to execution
• Represent marketing at leadership strategic meetings and intensives
• Serve as final decision-maker on all marketing related decisions
• Develop and execute the 12-month roadmap to hit $2.5M by end of 2026 and $4M+ by end of 2027.
• Identify and test new opportunities to scale (partnerships, channels, market segments)
• You will have a total marketing budget of 15-20% of topline revenue at all times.

Channel Optimization & Growth

• Maximize ROI on current working channels: referrals and events
• Accelerate growth on emerging channels: YouTube and email marketing
• Maintain target 1:10 CPA to LTV ratio across all channels
• Dial in messaging and pre-framing to attract ideal fit leads ($3-5M ARR minimum founders)
• Optimize lead quality for sales conversion rate into core offer (target minimum 40% conversion on inbound SQLs (our current average).

Evergreen Marketing Machine Building

• Build brand and growth strategy that creates sustainable, founder-independent marketing
• Install long-term strategies: SEO/AEO, strategic partnerships, evergreen funnels, brand positioning
• Establish clear transition path to marketing that doesn't require founder time as growth constraint
• Design systems that work while you sleep

M&A Market Penetration & Strategic Partnerships

• Work with CEO to test and develop offers for M&A buyers and sellers
• Build market penetration strategy through strategic relationships and joint ventures
• Position Spyglass as a key player in the M&A operations transformation space
• Identify and execute high leverage partnership opportunities

Team Building & Management

• Design and lead a lean, AI-enabled marketing team using mix of contractors, agencies, and tools
• Manage existing fractional team members and agency partners
• Own all hiring, management, and performance decisions for marketing team
• Maximize revenue per marketing dollar spent through smart resource allocation

Performance & Data Management

• Work with operations team to build and maintain marketing dashboards, attribution, and KPIs
• Review and optimize marketing tactics based on data weekly
• Make data-driven decisions about channel allocation and campaign performance
• Track leading and lagging indicators across all marketing activities

REQUIREMENTS (EXPECTED PROFICIENCIES)Experience Requirements (Non-Negotiable)

• Proven track record driving revenue growth in B2B digital service businesses, ideally in consulting, coaching, or professional services
• Demonstrated experience taking a business from $1 to $5M through strategic marketing leadership
• Hands-on expertise building and optimizing multiple marketing channels simultaneously
• Personal brand leverage experience. You understand how to strategically deploy a founder's personal brand while building scalable, founder-independent systems
• Partnership and JV marketing expertise. You've built strategic relationships that drove significant revenue
• Full-funnel marketing mastery from brand awareness to lead generation to sales enablement
• Team building experience. You've hired, managed, and optimized lean, high-performing marketing teams

Core Competencies

• Revenue ownership mindset: You see all marketing activity through the lens of revenue ROI and understand 2nd and 3rd order impacts on sales and client success
• Strategic AND tactical: You can toggle between 30,000 ft vision and 3 ft execution. You're both a thinker and a doer, willing to roll up your sleeves and execute your own ideas
• Gas pedal energy: You love fast iteration, MVP mindset, and lean marketing stack design. You ship, test, learn, optimize, repeat
• Metrics-driven decision making: You're obsessed with data and use it to inform every decision, not just report on what happened
• AI fluency: You embrace AI for execution efficiency and stay current on new tools that create leverage
• Creative collaborator: You work exceptionally well with leadership teams and translate effectively across different zones of genius
• Resource stewardship: You maximize outcomes with lean teams, scrappy experiments, and smart spend
• Exceptional project management: You juggle multiple concurrent initiatives while maintaining organization and follow-through

Critical Soft Skills (Deal-Breakers)

• Marketing mastery, not just competence: You're a true expert who has done this multiple times and can teach others. We're not hiring on potential, we're hiring on proven excellence
• Strategic understanding of personal brands: You grasp that Jhana's personal brand is a strategic asset, not a limitation. You know how to leverage founder brands to drive growth while building sustainability
• Mission-driven alignment: You genuinely care about helping purpose-based leaders scale their impact. This isn't just another marketing gig, it's about amplifying the good our clients do in the world
• Ownership mentality: You take radical ownership for outcomes, not just effort. When things go wrong, you look first at what you could have done differently
• Clear, direct communication: You embody "Van Talk," honest, mature, emotionally intelligent communication that serves shared goals
• Self-directed execution: You're comfortable with complete autonomy. You don't need hand-holding or constant direction. You see what needs to happen and make it happen
• Resilience and adaptability: You thrive in fast-changing startup environments where priorities can shift and you need to pivot quickly

Technical Requirements

• Deep platform knowledge: Expert level understanding of YouTube, email marketing, event marketing, referral systems, and partnership marketing
• Marketing tech stack proficiency: Experience with CRMs, marketing automation, analytics platforms, attribution tools, and AI marketing tools
• Budget management: Experience managing marketing budgets strategically (15% of revenue in our case)
• Remote work excellence: Proven ability to drive results in 100% remote environment
• Ability to work in US time zones for collaboration with North American leadership team

BENEFITS

• Compensation: 1099 contractor relationship with salary + performance-based compensation structure
• Possibility for revenue/profit sharing in the short term
• Equity opportunities in the long term for the right fit
• Marketing Budget: You'll have access to 20% of top-line revenue ($240K+ annual total marketing budget at current revenue)
• Autonomy & Flexibility:
• 100% remote work from anywhere
• Complete autonomy over your schedule and how you structure your work
• Unlimited time off policy: we manage based on outcomes, not hours
• Professional Growth:
• Professional development budget for courses, conferences, and learning
• Opportunity to connect with top digital marketers in the space
• Direct partnership with founder on high-level strategy
• Complete autonomy & ownership over an entire marketing function
• Impact & Ownership:
• True leadership role with decision-making authority
• Your work directly drives company revenue and transformation
• Opportunity to shape company trajectory during critical growth phase

HOW TO APPLY

If you are interested in this position, please submit an application at the following link
Our team will review your application and get back to you shortly. We look forward to hearing from you!

Job Type: Full-time

Benefits:

• Flexible schedule
• Paid time off
• Professional development assistance

Work Location: Remote