Creative Strategy Jobs in Boston, MA (NOW HIRING)

Company: CaseFoundry
Location: Remote — United States or Canada
Role Type: Independent Contractor
Compensation: Commission-Based Sales
Industry: Legal Marketing / Advertising Strategy
Target Market: Established Criminal Defense Law Firms

About CaseFoundry

CaseFoundry is a specialized creative performance consulting firm for established criminal defense law firms.

We help firms improve advertising performance by analyzing creative and campaign data, identifying what is working, building structured testing frameworks, and providing ongoing strategic guidance.

We work with firms that are already investing significantly in paid advertising and want to improve how they approach creative strategy, testing, campaign performance, and ongoing optimizations.

Our work is not traditional ad management or creative production. We act as a strategic partner to help law firms understand what is working, why it is working, what should be tested next, and how to build a more disciplined creative performance system. We sit at the intersection of creative strategy, paid-media performance, testing methodology, and business growth. 

We begin with a comprehensive strategic engagement followed by ongoing monthly advisory support.

We are building CaseFoundry as a focused, high-value consulting company rather than a high-volume marketing agency.

The Role

We are looking for an entrepreneurial Business Development & Sales Executive to help grow CaseFoundry's U.S. client base.

This is not an inbound-only sales role.

You will be responsible for identifying qualified criminal defense firms, reaching decision-makers, generating interest, and getting prospects to book a free initial consultation.

You may generate opportunities through:

• Cold outbound prospecting
• Email outreach
• Phone outreach
• LinkedIn and professional networking
• Existing relationships in the legal industry
• Existing relationships in advertising or marketing
• Referrals
• Conferences and industry events
• Strategic partnerships
• Direct outreach to law-firm owners and executives
• Your own professional network

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You may also join initial consultations when needed to help move qualified prospects toward a decision.

This role combines:

Prospecting + relationship building + qualification + consultative selling + closing support

Who We Sell To

Our ideal clients are established criminal defense firms that generally:

• Spend approximately $30,000+ per month on advertising
• Run established paid-media campaigns
• Have meaningful historical advertising data
• Have the ability to produce and test new creative
• Want to improve advertising efficiency and qualified case inquiries
• Have the resources to invest in premium strategic consulting

Typical decision-makers include:

• Law-firm owners
• Managing partners
• CEOs
• CMOs
• Marketing directors
• Heads of growth

What You Will Be Selling

CaseFoundry engagements include:

• Creative performance audits
• Paid-media campaign audits
• Analysis of historical and active creative
• Creative testing frameworks
• Prioritized testing roadmaps
• Strategic recommendations
• Ongoing campaign and creative analysis
• Twice-monthly strategy sessions
• Implementation and performance guidance

You do not need to be a media buyer, but you should be able to understand and confidently discuss advertising performance, customer acquisition, cost per lead, creative testing, and marketing economics.

Core Responsibilities

• Prospecting & Business Development
• Identify qualified criminal defense firms
• Research decision-makers
• Conduct cold outbound
• Leverage existing relationships where applicable
• Generate referrals and introductions
• Build and maintain a qualified pipeline
• Consistently create conversations with potential clients

Qualification

Determine whether prospects are a strong fit based on factors such as:

• Advertising spend
• Current marketing activity
• Firm size
• Business need
• Ability to implement recommendations
• Budget
• Decision-making authority
• Timing

We care more about qualified opportunities than meeting volume.

Initial Consultations & Closing Support

Help qualified prospects book a free consultation.

You may be required to participate in consultations to:

• Build rapport
• Ask discovery questions
• Address commercial questions
• Handle objections
• Clarify value
• Help establish next steps
• Support the close

CaseFoundry leadership or strategy personnel may lead the deeper strategic portion of the consultation.

Pipeline Management

Maintain accurate records of:

• Prospects
• Conversations
• Consultations booked
• Follow-ups
• Opportunities
• Deals won and lost
• Revenue generated

You will also provide feedback on common objections, pricing reactions, market trends, and reasons deals are won or lost.

What Happens After the Sale

Once a client signs, the account is transitioned to the CaseFoundry strategy team.

The delivery process currently includes:

• One-hour onboarding session
• One-hour audit and analysis session
• Two one-hour strategy sessions per month
• Ongoing performance, testing, implementation, and strategic support

You are not responsible for delivering the consulting engagement.

Ideal Candidate

We are looking for someone who is:

• Experienced in B2B business development or sales
• Comfortable generating their own pipeline
• Confident with cold outbound
• Comfortable speaking with senior executives and business owners
• Strong at consultative selling
• Persistent without being aggressive
• Comfortable discussing five-figure investments
• Organized and disciplined with follow-up
• Able to operate independently
• Commercially minded
• Ethical and professional

Preferred experience includes:

• High-ticket B2B sales
• Consulting sales
• Agency sales
• Digital advertising sales
• SaaS sales
• Legal-industry sales
• Professional-services sales

Experience selling $10,000+ engagements is strongly preferred.

Experience selling $20,000–$100,000+ services or solutions is particularly relevant.

Experience or relationships within legal marketing, criminal defense, paid media, advertising agencies, or legal technology are especially valuable.

Independent Contractor Structure

This is a commission-based independent contractor opportunity.

The contractor will operate with substantial independence in how they organize and execute their business-development activities while representing CaseFoundry professionally.

Payment timing, attribution rules, commission eligibility, and other engagement terms will be outlined in the independent contractor agreement.

Compensation

Our current compensation structure is as follows:

30% ($5,550 USD) of the $18,500 USD initial engagement fee

plus

10% ($400 USD) of each $4,000 USD monthly strategic-support payment for up to 365 days from the client’s initial onboarding date

Recurring commission applies only while the client remains active and is limited to the first 365 days of that client relationship. It ends after 365 days even if the client continues working with CaseFoundry.

A standard client retained for the full first year represents $10,350 USD in total commission: $5,550 from the initial engagement fee plus up to $4,800 in recurring commission.

Payment timing, attribution rules, and any additional commission terms will be outlined in the independent contractor agreement.

As CaseFoundry grows, future sales roles may also be offered under a base salary + commission structure.

Performance

Success will be measured primarily by:

• Qualified consultations booked
• Qualified opportunities generated
• New clients originated
• Revenue generated
• Consultation-to-client conversion
• Pipeline quality
• Follow-up effectiveness

We are looking for revenue-producing activity, not activity for its own sake.

Why CaseFoundry

CaseFoundry is being built as a specialized, high-value consulting company rather than a high-volume marketing agency.

Early sales team members will have the opportunity to help shape the company's sales process and potentially grow into roles such as:

• Senior Business Development
• Enterprise Sales
• Strategic Partnerships
• Sales Leadership

How to Apply

Please submit:

• Resume or professional background

We equip criminal defense firms with a framework for
high-performing creative, audit their existing creative and
campaign performance, and build a structured testing roadmap
that shows your team what to create, test, and improve next.