Head of Sales | Strategy, Advisory & Enablement

JumpSeat; Chicago (IL); Hybrid; USD 80,000 - 150,000; Full time

Job summary

Join a forward-thinking company as the Head of Sales Strategy, Advisory & Enablement, where you'll shape impactful sales strategies and enablement programs. This role offers the chance to work closely with clients to enhance their revenue generation through innovative go-to-market strategies and effective sales processes. Collaborate with a dynamic team in a remote-first environment, where your contributions will drive significant client success. Enjoy a supportive culture with a yearly development budget, unlimited PTO, and unique rewards like an anniversary flight. If you're a strategic thinker passionate about sales, this is the opportunity for you!

Benefits

Yearly Development Budget

Anniversary Flight

Unlimited PTO

Summer Fridays

Daily Recognition Program

Qualifications

• 5-10 years experience in sales roles, including quota-carrying positions.
• Strong knowledge of outbound campaign design and execution.

Responsibilities

• Define and evolve Sales Advisory offerings focused on demand generation.
• Lead client workstreams for sales audits and GTM strategy design.

Skills

Sales Strategy & Execution

Outbound Campaign Design

Strategic Thinking

Problem Solving

Interpersonal Skills

Education

Bachelor's Degree

Tools

Salesforce

HubSpot

Outreach

Job description

Head of Sales Strategy, Advisory & Enablement JumpSeat exists to eliminate random acts of sales and marketing.

JumpSeat is a hybrid creative agency advisory organization. We work alongside B2B marketing and revenue-generating teams in the US to drive financial growth and success for our clients across various business focus areas, including sales, marketing, business development, partnerships, operations, and enablement.

We are seeking a versatile Head ofSales Strategy, Advisory & Enablement to join our Sales Advisory Capability, to work side by side with our leadership to guarantee the successful delivery of impactful sales strategies and enablement programs.

You’ll have the opportunity to make a significant impact by helping our clients achieve quota attainment through smarter go-to-market strategies, effective outbound motions, and well-designed sales processes. You will be a key driver in shaping our Sales Advisory offerings and ensuring our deliverable quality is exceptional.

What to expect about this role:

• Continue to Build our Sales Capability
  You’ll take us to the next level—defining, shaping, and evolving our Sales Advisory offerings with a sharp focus on demand generation, sales process design, and revenue acceleration.

• Drive Client Engagements
  Lead client workstreams that span sales audits, outbound campaign execution, and GTM strategy design.

• Master Agile GrowthOS
  Learn and apply our proprietary Agile Growth OS to help clients adopt iterative, focused, and scalable approaches to growth.

• Design Outbound Campaign Strategy
  Lead the development of outbound/email campaign strategies—guiding messaging, sequencing, targeting, and channel planning.

• Be a Trusted Advisor
  Sit at the table with senior client stakeholders to solve sales challenges, design smarter systems, and coach teams through change.

• Operationalize Sales Strategy
  Turn sales strategy into action for client BD and sales teams—whether it’s new cadences, better handoffs, or rethinking incentive structures.

• Contribute to Thought Leadership & IP
  Codify frameworks, write POVs, and help turn practical experience into a scalable methodology.

• Grow the Team and Culture
  Mentor emerging talent, collaborate across practices, and help build a culture of curiosity and performance.

Our ideal candidate has:

•Experience in Sales Strategy & Execution with 5–10+ years in sales-related roles, including at least 2+ years successfully prospecting and 2+ years in a quota-carrying sales role, or equivalent work experience.

•Strong knowledge of outbound campaign design and execution with proven experience, successfully supporting client sales teams.

•Excellent strategic thinking and problem-solving skills, with the ability to prioritize and multitask across client engagements.Exceptional communication and interpersonal skills, enabling effective collaboration with diverse stakeholders.

•Growth-minded and entrepreneurial approach with the ability to adapt to changing client needs and work independently.

•Familiarity working with modern sales stacks like Salesforce, HubSpot, and Outreach is required.

What is in it for you?

We’re a fast-growing team inside a bold, values-driven company.

You’ll have the chance to:

• Shape a high-impact capability from day one.

• Work on genuinely interesting client problems.

• Grow alongside smart, kind people.

•You’ll join a remote-first company with colleagues in the US, Italy, and Argentina.

•You’ll find a place to grow and develop: we support all our crew members with a yearly $1000 Development Budget

•We celebrate you: on your first anniversary, you’ll receive a $500 Anniversary flight to go anywhere in the world

•We recognize each other: We leverage Hey Taco for our daily recognition. We also have a great rewards program associated with it!

•We thrive in balance: Unlimited PTO, Summer Fridays, Time off between holidays? You name it, we’ve got it.

Are you a motivated sales strategist with a passion for helping clients achieve their revenue goals? Perhaps an experienced sales leader looking to leverage their expertise in an advisory capacity? We want to talk to you. We want the strategic thinkers, the experienced practitioners, the growth-oriented individuals.