Head of Copy + Content

Crackerjackcom; Boston (MA); Hybrid; USD 100,000 - 150,000; Full time

Job summary

Crackerjack is seeking a senior creative and content leader in Boston to steer editorial standards, strategy, and high‑impact storytelling across campaigns, brand narratives, thought leadership, and client communications.

You’ll mentor a team of writers, shape creative direction, and stay hands‑on with craft, delivering work that is as precise as it is persuasive, while partnering with a broader team of designers, strategists, and account colleagues.

Qualifications

• 10+ years of experience in copywriting, content development and leadership.
• Proven track record of leading creative work and people.
• Significant financial services experience (retirement, investments, insurance) and regulatory awareness.
• Portfolio demonstrating range: headlines, video scripts, websites, long-form content.
• Exceptional editing skills to strengthen arguments, structure and voice.
• Strong strategic instincts aligning business goals with audience needs.
• Diplomacy to challenge conventional thinking and propose alternatives.
• Understanding of brand strategy and integrated marketing with measurable impact.
• Experience working with senior‑level clients and managing competing priorities.
• Intellectual curiosity, judgment, and commitment to getting the work right.
• Generous spirit, sense of humor, and genuine love for the craft.

Responsibilities

• Lead strategic and editorial direction across copy and content work; set a high bar and ensure client objectives are met.
• Manage complex projects from kickoff to final delivery, making sound judgments to keep work moving forward.
• Turn strategy and audience insights into compelling concepts, campaigns, and brand narratives.
• Collaborate with design, strategy, and account teams to harmonize thinking from early concept to execution.
• Mentor writers and develop editorial standards to raise the quality of work.
• Write across formats: headlines, posts, scripts, websites, white papers, and thought leadership.
• Edit for stronger arguments, sharper structure, and consistent voice.
• Champion audience needs and ensure clarity of why clients should care.
• Present recommendations with clarity and defend the thinking behind them.

Skills

10+ years copywriting

Leadership experience

Financial services experience

Portfolio quality

Editing skills

Strategic instincts

Brand strategy understanding

Senior client experience

Communication curiosity

Judgment

Humor and craft

Job description

Location: Hybrid (M-W in office; remote Th-F)

Job Type: Full-time

Post Date: October 26, 2026

We’re looking for a writer’s writer. A sharp editor. A big thinker. Someone who can find the interesting angle in the seemingly ordinary—and make other people care about it, too.

Someone who gets just as excited about a brilliant three-word headline as a beautifully constructed 1,500-word article. Who can turn a complicated financial product into a compelling story, make a nonprofit’s mission come alive, or uncover the one fascinating insight buried in 40 pages of research.

And someone who knows how to bring out the best in other writers, too.

Crackerjack is a Boston-based marketing and communications agency working with organizations across financial services, retirement, insurance, higher education, healthcare, the nonprofit space, and more.

Yes, we write about investments, retirement plans, and insurance products. We also create campaigns, launch brands, tell remarkable stories, and help organizations communicate things that make people’s lives better.

We believe even the most technical subject deserves a story worth telling—and creative that brings it to life.

The opportunity

We’re looking for a senior creative and content leader with exceptional writing and editing skills, sharp strategic instincts, and a knack for finding the idea that makes everything click.

You’ll help set the creative and editorial standard for our agency, bringing a strategic lens to everything from major campaigns and brand narratives to thought leadership, websites, and everyday client communications. You’ll see the big picture, connect the dots, and make sure the work doesn’t just sound great—it accomplishes something.

You’ll partner with our Creative Director and Associate Creative Director of Copy, working alongside an established group of writers, designers, strategists, and account colleagues. You’ll bring another level of strategic thinking, editorial excellence, and creative direction to the work we do together.

You know that what a client asks for and what they actually need aren’t always the same thing. You ask good questions, challenge assumptions, and have the judgment to recommend a different approach when there’s a smarter way forward.

And you believe in giving clients a little more than they expected. An unexpected insight. A fresh perspective. A creative twist that makes the work that much better. We call those the sprinkles. And boy, do we love sprinkles.

You’ll mentor writers, guide complex assignments, shape creative direction, and take responsibility for the quality of the work. You’ll also write. Because while this is very much a leadership role, we want someone who still loves the craft and isn’t afraid to roll up their sleeves.

What you’ll do

• Lead the thinking. Provide strategic and editorial leadership across our copy and content work. Set a high bar, guide creative direction, and ensure the work delivers on the client’s objectives—not just the assignment.
• Take ownership. Lead complex projects from the first conversation to the final deliverable, bringing sound judgment, initiative, and the ability to make decisions that keep the work moving forward.
• Find the big idea. Turn strategy, research, and audience insights into compelling concepts, campaigns, and brand narratives that connect with the people they’re meant to reach.
• Look beyond the assignment. Get to the heart of what the client is trying to accomplish. Ask the questions others might not, identify opportunities they may have overlooked, and recommend a different path when it will deliver a stronger result.
• Write brilliantly. From advertising headlines, social posts, and video scripts to websites, executive communications, white papers, and thought leadership. You’ll be hands‑on with some of our most challenging and high‑profile assignments.
• Edit like you mean it. Go well beyond grammar and punctuation. Strengthen the argument, sharpen the structure, refine the voice, and make every word earn its place.
• Make good writers even better. Coach and develop writers, provide thoughtful editorial direction, and help build a culture where feedback is generous, standards are high, and the writing keeps getting stronger.
• Make the complex compelling. Get curious. Interview experts. Dig into the research. Find the gold others might miss—and turn it into something audiences actually want to read.
• Champion the audience. Never lose sight of the person on the receiving end. What do they need to know? Why should they believe it? And the big one: Why should they care?
• Create across disciplines. Work closely with design, strategy, and account colleagues from early thinking through final execution. Bring people together, build on one another’s strengths, and help the best thinking win.
• Bring ideas to life. Present recommendations with clarity and confidence, explain the thinking behind them, and navigate feedback to reach the best possible outcome.
• Sweat the details. Accuracy, brand voice, consistency, and deadlines matter. So does getting the little things right. Every time.

What you’ll bring

• 10+ years of experience in copywriting, content development, and creative leadership, ideally in an agency environment.
• A proven track record of leading creative work and people. You’ve guided writers, directed complex projects, established editorial standards, and been accountable for the quality of work produced by others—not just your own.
• Significant financial services experience. You’ve written extensively about financial services, retirement, investments, or related industries. You understand the subject matter, the nuances, and the responsibility that comes with getting it right, including compliance and regulatory considerations.
• A portfolio that makes us stop scrolling. Smart concepts. Great headlines. Standout video scripts, websites, and social posts. Newsletters, brochures, white papers, and beautifully crafted long‑form content. Show us range, strategic thinking, and a way with words.
• Truly exceptional editing skills. You can spot a weak argument, a missed opportunity, or a muddled message from a mile away—and you know how to fix it.
• Strong strategic instincts. You can connect business objectives, audience needs, and creative execution—and recognize when an assignment calls for a different approach.
• The tact and diplomacy to challenge conventional thinking. You can offer a thoughtful alternative, persuade stakeholders, and recognize when the original direction is exactly right.
• A strong understanding of brand strategy, storytelling, and integrated marketing, and how content contributes to measurable business results.
• A track record of working with senior‑level clients, navigating feedback constructively, and managing competing priorities.
• Intellectual curiosity, sound judgment, and an keen commitment to getting the work right.
• A generous spirit, a sense of humor, and a genuine love for the craft.

A little about us

We’re a close-knit team of smart, creative, hardworking people who genuinely like each other. We take the work seriously. Ourselves? Not so much.

We believe good ideas can come from anywhere. We value curiosity over ego, generosity over hierarchy, and people who care enough to improve something that’s already pretty good.

We solve problems for clients who count on us to think, not just execute. Some assignments are clearly defined; others take shape through the questions we ask and the solutions we develop.

And we believe there’s no such thing as a boring assignment. Sometimes the most rewarding challenges come in the least glamorous wrapping. That’s part of the fun.

And yes, we have a genuinely great culture. Lots of laughs. Good people. And an office snack situation that deserves its own paragraph. (But we’ll show some restraint.)

Our hybrid schedule: We’re in our bright (and very orange!) Boston office, right across from South Station, Monday through Wednesday. Thursdays and Fridays, we work remotely.

Important note: This is a hybrid position requiring three days a week in our Boston office. You could be the greatest writer, editor, and creative leader on the planet, but if you’re looking for a fully remote job, please don’t apply. We promise we’re not going to change our minds. Even for you.