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One of the coolest marketing jobs around!

HARRY COMMENTS: We are working with a tremendously cool financial services firm to help them find a new VP of Media – Awareness and Consideration.

Our client is the leading reverse mortgage lender in America. They’re a publicly traded company (NYSE) generating over $300 million in annual revenue, with nearly 9,000 loan originations totaling close to $2 billion in 2024.

With 750+ employees and nearly $30 billion in assets under management, they’ve established themselves as the trusted name in helping seniors unlock their home equity.

But here’s what makes this opportunity special: they’re in the middle of a dramatic transformation.

Fifteen months ago, the company brought in a new Chief Customer Officer—a proven digital commerce leader with experience scaling businesses at Amazon, Petco, and Neiman Marcus. He grew Petco’s digital business from sub-$100M to over $400M and increased EBITDA by 10x. Now he’s doing the same thing here, and he’s building a world-class team to help her execute.

Historically, the company has been great direct response marketing, bottom-of-funnel conversion, and managing broker relationships.

What they haven’t been very good at is deeply understanding their customers and creating an integrated end-to-end experience that is brand-accretive, personalized and digital.

That’s changing fast.

Six months ago, the client launched paid social advertising, and just three months ago, they launched streaming/CTV. Monthly spend has grown from $5,000 to $80,000 in just six months. The board has given the green light to continue scaling aggressively, and they need someone who can take these nascent channels and turn them into meaningful revenue drivers.

That’s where YOU come in.

This is a 100% remote company. The CCO is based in San Diego, and team members are spread all over the US: East Coast, Texas, Utah and everywhere in between. The firm has embraced remote work as a core part of its culture, giving employees the flexibility to live where they want while doing their best work. Let’s talk about that …

What’s Working:

• Unlimited marketing budget if you can prove incremental growth (no fixed caps—chase growth wherever you find it)
• New leadership team focused on brand building, storytelling, customer, digital transformation
• Strong financial position after turning profitable in 2024 following industry-wide challenges in 2022-2023
• Market leadership position and brand recognition in the reverse mortgage space
• Willingness to invest in people, technology, and capabilities to win

What’s Challenging:

• This is a company learning to think digitally. As the CCO puts it: “This company has never really done optimization because frankly, we didn’t have a digital mindset.”
• Historically siloed organization where each channel operated independently without cross-functional collaboration
• The team is very direct-response focused and will need education on how mid-funnel channels contribute beyond last-click attribution
• Creative production has been a bottleneck (low volume, inconsistent quality), though this is actively being solved
• Attribution infrastructure is immature: Currently, you can’t track someone who sees a social ad then converts via organic search. This is a big focus in 2026

The CCO is being honest about these challenges because he wants someone who thrives on building, not just managing. If you need perfect infrastructure and mature processes, this isn’t your gig.

But if you get energized by the opportunity to build something from scratch and see your impact on the business, you’ll love it there. Think of the firm as a hybrid of a startup in its DNA (bias for action, hypothesis-driven testing, moving fast) and a large company (financial stability and proven market)

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ABOUT THE INDUSTRY

You’ll be marketing reverse mortgages to American homeowners age 55 and older. Let’s be clear about what this product is and why it matters.

A reverse mortgage allows seniors to convert their home equity into cash without selling their home or making monthly mortgage payments. Over 1.3 million seniors have used this loan to access their home equity.

Instead of paying the bank every month like a traditional mortgage, the bank pays them. The loan doesn’t have to be repaid until they move out permanently, sell the home, or pass away.

For “house-rich, cash-poor” seniors—people sitting on valuable homes but living on tight retirement budgets—this product can be life-changing.

The Market Opportunity:

The addressable market is massive and growing. America is aging rapidly, and there are tens of millions of homeowners over 55 with significant home equity who don’t realize they can access it. The three most common reasons seniors get reverse mortgages are:

1. Need monthly cash to cover living expenses beyond what Social Security provides
2. Medical bills and healthcare costs eating into retirement savings
3. Home renovations and repairs to age in place comfortably

My client originated nearly 9,000 reverse mortgages in 2024, with a profit per loan at origination of roughly $31,000 (through origination fees of $2,500-$6,000, interest rate spreads of about 2.75%, ongoing servicing fees, and securitization). Meaning, this is a VERY high-value product with excellent lifetime economics!

The Marketing Challenge:

This is not an impulse purchase. The average customer is 73-75 years old, predominantly a single woman with monthly retirement income around $2,400 and a home worth $200,000+ with substantial equity. The decision-making process takes weeks or months, not hours or days. As the CCO says: “You’re selling a complex product, and a loan won’t close in 24 hours. These things take a little time.”

Normally, a customer’s journey involves seeing ads, researching online, talking to family members (especially adult children who often have concerns), speaking with a loan officer, going through mandatory counseling, and finally deciding. Your job is to get them into the top of that funnel by building awareness and aiding consideration.

The Regulatory Environment:

Now that you understand the mandate, here’s what makes this role intellectually stimulating: Fair lending laws prohibit the targeting tactics you’re used to in consumer marketing. You cannot use lookalike modeling based on existing customers, nor can you target by gender, ethnicity, or wealth indicators.

This eliminates roughly 50% of the standard Facebook/ targeting toolkit.

You must succeed with interest-based targeting (people interested in retirement planning, home improvement, financial advice), contextual targeting (placing ads on retirement-focused content), and first-party data (your own customer lists for remarketing).

This constraint forces creativity and strategic thinking, and every ad must be reviewed and approved by the compliance team before it runs. You’ll need to build efficient workflows to get regulatory sign-off without slowing down your testing velocity.

The Competitive Landscape:

Your client competes with about a dozen major reverse mortgage lenders, including Mutual of Omaha (currently the largest), Longbridge Financial, PHH Mortgage, and Guild Mortgage. The company is consistently one of the top two originators in the country, with an A+ BBB rating and 4.7-star customer reviews.

But here’s the thing: as the CCO notes, ““Our industry isn’t as far on the digital maturity curve as other industries like Retail. Also, it often forgets that our customers are also consumers of other brands and thus have ever-raising expectation on how to engage them and what is a “good” experience.”

If you come from a digitally sophisticated consumer brand, you’ll have playbooks and capabilities your competitors simply don’t have. That’s a competitive advantage.

The Market Headwinds:

Reverse mortgages carry stigma from the “Wild West” days of the early 2000s before government regulation cleaned up the industry. Many people—including adult children of potential customers—harbor negative perceptions. Part of your job is storytelling that educates, builds trust, and removes those barriers.

You’re also competing with alternatives: home equity loans, HELOCs, credit cards, and “doing nothing.” Your messaging needs to clearly articulate why a reverse mortgage is the right solution for specific customer situations.

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ABOUT THE ROLE

The Opportunity

You’re being hired to build and scale the company’s awareness and consideration marketing engine. Specifically, you’ll own paid social media and streaming/connected TV advertising—two channels the company launched just 3-4 months ago that are showing promising early results.

Your mandate is straightforward: double or triple the revenue from these channels in 2026 while building the measurement frameworks that prove their incremental contribution to the business. If you succeed, you’ll unlock millions in additional marketing budget and position the company as a best-in-class digital advertiser in financial services.

You’ll manage a team of three (a Director focused on social/CTV strategy, a Streaming Media Manager, and a Campaign Manager), with the ability to add headcount as the business scales. The CCO has made it clear: if you can prove incremental growth, budget is unlimited. The company will chase growth wherever you find it.

This is a player-coach role for the first 6-12 months. You’ll need to be hands-on in campaign setup, vendor negotiations, creative review, and analytics. As the channels mature and your team develops, you’ll transition to pure leadership—setting strategy, managing stakeholders, and evangelizing the role of mid-funnel marketing to the executive team.

What You’re Walking Into …

The Good:

• Nascent but high-growth channels showing strong early traction (5x spend increase in 6 months)
• Unlimited budget if you can demonstrate incremental growth
• Creative bottleneck being actively solved as you join (more volume, better quality on the way)
• Two-thirds of your team already hired (Director + Campaign Manager + Streaming Manager mostly in place)
• New CMO just started who will help with brand positioning and cross-channel storytelling
• Executive leadership committed to digital transformation and willing to invest

The Challenging:

• Attribution infrastructure is immature—you’ll be “building the plane while flying it”
• Company culture is heavily direct-response focused; you’ll need to educate others about “brand metrics” that don’t show immediate ROAS
• Organization has been siloed historically; cross-functional planning is more immature than at most companies. However all teams are yearning to create an integrated experience
• You may inherit a Director hired in parallel to your search (the CCO values speed over perfect sequencing)
• Creative production is improving but still developing

The CCO is looking for someone who gets energized by these challenges, not discouraged by them. If you need perfect conditions to do great work, this isn’t your role. But if you thrive in environments where you can make a disproportionate impact because you’re bringing capabilities the organization doesn’t have yet, you’ll love this.

Requirements: Can You Win in This Role?

Must-Haves (Non-Negotiable):

1. 10+ years of digital marketing experience, with at least 5 years specifically managing paid social and streaming/CTV campaigns at scale
2. Client-side experience building nascent channels from scratch—you’ve taken a channel from zero or near-zero and scaled it to meaningful business contribution. This is not a role for agency folks who’ve only managed mature programs.
3. Proven track record in complex, considered-purchase categories—you’ve marketed products that require education, have long sales cycles (weeks/months), and involve multiple decision-makers. Bonus points for financial services, insurance, healthcare, or high-ticket home services.
4. Mid-funnel measurement expertise—you know how to implement brand lift studies, incrementality testing, Marketing Mix Modeling, and view-through attribution. You can educate executives on contribution beyond last-click.
5. Leadership experience managing and developing teams—you’ve built teams, managed poor performers, and developed people for long-term growth (not just task execution).
6. Exceptional cross-functional collaboration skills—you’ve succeeded in matrixed, complex organizations where success required building relationships across marketing, product, analytics, finance, and executive leadership.
7. Experience in highly regulated industries—you understand compliance workflows, have worked within legal/regulatory constraints, and know how to move fast within guardrails.

Strongly Preferred:

1. Experience marketing to seniors (55+) or understanding age-related user behavior and media consumption
2. Background in financial services, lending, insurance, or other trust-intensive categories
3. Track record of creative strategy and high-volume production management
4. Experience with programmatic advertising, DSPs (The Trade Desk, DV360), and publisher-direct deals
5. Comfort with ambiguity, building processes from scratch, and operating without perfect infrastructure

You’re Not Right for This Role If:

• You need sophisticated attribution systems and mature processes before you can operate
• You’re uncomfortable educating and influencing skeptical colleagues who question mid-funnel spend
• You prefer to stay in your lane rather than build cross-functional relationships
• You’ve only worked at agencies (not client-side) or only managed mature channels at scale
• You need a large team and perfect creative production pipelines from day one
• You’re looking for a pure strategy role—this requires rolling up your sleeves for at least the first year

Responsibilities: What Success Looks Like

Your performance will be measured across six dimensions:

1. Channel Growth & Scale Execution (30% of your job)

Drive 2-3x growth in opportunities from paid social and streaming/CTV in 2026:

• Scale monthly media spend from $80K baseline to $200K-$300K+ as you prove incremental growth
• Launch and scale CTV from infancy across programmatic (The Trade Desk, DV360), publisher-direct deals (Hulu, Roku, Paramount+), addressable TV, and OTT platforms
• Expand paid social across , LinkedIn, TikTok, potentially Reddit, Pinterest, and emerging platforms
• Build organic social presence from scratch (community management, influencer programs, always-on content)
• Establish repeatable playbooks for audience targeting, creative testing, and budget allocation

2. Measurement, Attribution & ROI Accountability (25% of your job)

Build the frameworks that prove your channels’ contribution and unlock budget:

• Implement brand lift studies, incrementality testing (geo holdouts, matched market tests), and view-through attribution
• Partner with analytics team to build Marketing Mix Modeling that quantifies total business impact
• Define and track mid-funnel KPIs: reach, brand awareness, aided recall, engagement, consideration lift
• Educate CEO, CFO, and board on how awareness channels contribute beyond last-click ROAS
• Create forecasting models and budget allocation frameworks tied to business outcomes

Current state: Cost per opportunity is approximately $1,000, with an LTV:CAC ratio of 1.5:1. There’s room for optimization, but the priority is scale first, then efficiency.

3. Creative Strategy & Execution Excellence (20% of your job)

Build a high-volume, high-quality creative engine that overcomes stigma and drives response:

• Partner with creative team to produce multiple ad variations per week (not one video per month)
• Develop storytelling frameworks that address top customer needs: monthly income, medical bills, home renovation
• Create platform-specific creative (what works on ≠ TikTok ≠ CTV)
• Establish continuous feedback loops: daily/weekly performance review → insights to creative team → next batch incorporates learnings
• Navigate compliance efficiently to maintain testing velocity
• Follow best-in-class examples (the CCO specifically mentioned Rocket Mortgage’s variety and non-stale creative approach)

Key constraint: You cannot use demographic targeting. Your creative must be effective through interest-based and contextual placement alone.

4. Cross-Functional Collaboration & Influence (15% of your job)

Break down silos and become an internal evangelist for mid-funnel marketing:

• Build strong relationships with VP of Performance Marketing (who owns bottom-funnel), VP of Analytics, Product/UX, Finance, and Compliance
• Educate stakeholders on customer journey complexity: “It’s a fairly complex product… very unlikely to do all this in 24 hours”
• Partner with loan officers to mine customer insights for creative and targeting strategies
• Align paid campaigns with brand positioning and CMO’s storytelling initiatives
• Teach, don’t tell: bring data stories (brand lift results, incrementality proof, MMM findings) when executives question spend

The CCO explicitly asks candidates: “How do you create relationships? What was your most challenging relationship and how did you solve it?” This signals relationship-building is harder here than at most companies.

5. Team Building, Leadership & Talent Development (5% of your job in Year 1, growing over time)

Develop your three-person team and build organizational capability:

• Ramp and develop your Director of Social/CTV (potentially hired before you—may need to manage up or out quickly)
• Coach Streaming Media Manager and Campaign Manager to become strategic, not just tactical
• Instill “always be testing” culture and rigorous experimentation mindset
• Plan for future hiring as channels scale (if spend triples, you’ll need more bodies)
• Transition from player-coach (first 6-12 months) to pure leadership (year 2+)

The CCO’s leadership expectations: Can you define clear direction and roadmap for your team? Can you build high-performing teams with clear RACI, KPIs, and accountability? Can you develop your team into SMEs to educate the broader organization on latest trends and insights in that space?

6. Strategic Positioning & Thought Leadership (5% of your job)

Position the company as a best-in-class advertiser in financial services:

• Bring external best practices from prior client-side roles
• Stay ahead of platform evolution, new partnerships, and emerging tools
• Share cutting-edge measurement approaches (attention metrics, brand lift methodologies)
• Eventually: speak at industry conferences, contribute to trade publications, make the company a case study

Red Flags: What Could Derail You?

🟥 Attribution Infrastructure Is Immature

For now, the company can’t track cross-channel journeys. You must simultaneously scale AND build measurement. Mitigation: Use holdout tests, incrementality studies, and brand lift surveys while longer-term Marketing Mix Modeling is built.

🟥 Company has been historically very direct response focused

You’ll may face some skepticism about “brand metrics” that don’t show immediate ROAS. This is a “change management” challenge as much as an analytics one. Mitigation: Proactively educate with data stories, show quick wins, tie everything back to business outcomes.

🟥 Historically, Creative Has Been a Bottleneck

No doubt about it, the storytelling can be improved, and everyone knows it. You’re walking into an organization learning this capability. Mitigation: Plan to source external creative partners, agencies, or freelancers during ramp-up.

🟥 You Cannot Use Lookalike Modeling or Demographic Targeting

Fair lending laws eliminate 50%+ of standard social media targeting. Sorry. You must succeed with interest-based and contextual targeting only. Mitigation: This is a constraint you must accept and work within; no workarounds.

🟥 Company Is Historically Siloed

Cross-functional collaboration is a reality of this role. Political navigation is 50% of success. Mitigation: Invest heavily in relationship-building from day one, share learnings proactively, build trust through transparency.

🟥 You May Inherit a Director Hired in Parallel

If there’s a skill/chemistry mismatch, you’ll need to manage up or out quickly. Mitigation: Try to get involved in Director hiring if timing allows; if not, establish clear expectations and KPIs in first 30 days.

🟥 Market Volatility (Company Revenue Dropped 97% from 2021-2022)

Mortgage lenders live and die by interest rates. If markets crash, budgets could be cut mid-campaign. Mitigation: Build proof of performance quickly (90 days), document achievements, maintain flexibility.

What Success Looks Like at 100 Days:

The CCO will evaluate you on two dimensions: numbers and culture fit.

The Numbers:

• Opportunities from social/CTV channels are trending toward 2-3x growth trajectory (leading indicators show you’re on pace)
• Current cost per opportunity of ~$1,000 is maintained or improving as you scale
• You’ve established baseline measurement frameworks (brand lift studies launched, incrementality tests in-flight)
• Creative production velocity has increased meaningfully (multiple ad variations per week in market)
• You’ve identified and begun scaling the highest-potential platforms/tactics

The Culture & Relationships:

• You’ve earned respect and trust from teammates across marketing and beyond
• You’re viewed as a great partner—helpful, transparent, collaborative, not territorial
• Executives see you as someone who educates and informs, not just requests budget
• Your team feels developed and supported, not just managed
• You’ve built efficient compliance workflows that enable speed without breaking rules

Applications for this job are being coordinated by . To apply, CLICK HERE. Candidates, please be sure to email Harry for additional information that will differentiate you in your candidacy. Due to the intensely competitive nature of this search, thorough preparation for these interviews with this proprietary material is strongly recommended.