Vice President, Sales

Walker Sands • Chicago, IL

14d • Hybrid

About The Position

We strongly encourage people of color, lesbian, gay, bisexual, transgender, queer and non-binary people, veterans, parents, and individuals with disabilities to apply. As an equal opportunity employer Walker Sands is committed to diversity, equity, and inclusion and welcomes everyone to our team. In your application, please feel free to note which pronouns you use (For example – she/her/hers, he/him/his, they/them/theirs, etc). If you need reasonable accommodation at any point in the application or interview process, please let us know. Walker Sands is seeking a strategic, relationship-driven Vice President of Sales to accelerate our growth with enterprise B2B organizations within our target ICP. This senior leader will own our largest and most complex new business opportunities, guiding inbound enterprise prospects through the sales funnel while also leading a proactive outbound motion targeted at executive buyers in high-value accounts. In close partnership with our marketing team — particularly on account-based marketing (ABM) initiatives — this role will help shape and execute coordinated outbound strategies that build awareness, spark interest and create momentum with priority enterprise accounts. This role is ideal for a senior seller with deep agency, marketing or professional services experience who understands how to sell integrated, cross-disciplinary marketing programs in complex environments. Success in this role requires the ability to collaborate seamlessly across marketing, client services, strategy and operations, bringing diverse internal teams together to deliver compelling, outcome-focused solutions for enterprise buyers. Reporting to the SVP, Head of Growth, this role sits at the center of our agency’s GTM engine. You will manage other sellers (1-3 over time), partner closely with internal leaders across the organization, and serve as the executive point of contact for high-impact pursuits.

Requirements

• 10–15+ years of progressive B2B sales experience, ideally in marketing, consulting, or other professional services.
• Proven success closing complex integrated marketing deals with multi-stakeholder committees.
• 5+ years managing sales talent (BDRs, AEs, or Directors).
• Exceptional strategic thinking and executive communication skills, both written and verbal.
• Strong understanding of B2B buyer behavior, go-to-market motions and demand-generation practices.
• Ability to translate business needs into compelling, tailored proposals.
• History of strong performance in a fast-paced, goal-driven environment.

Nice To Haves

• Deep experience in B2B technology or other industries aligned with Walker Sands’ portfolio.
• Familiarity with Salesforce CRM, LinkedIn Sales navigator, as well as sales enablement softwares.
• Familiarity with outcomes-based marketing methodologies and integrated campaign models.
• Experience working closely with marketing teams to shape positioning and go-to-market strategies.
• Strong network within PE ecosystems or enterprise B2B communities.

Responsibilities

• Own revenue targets for enterprise new business, with a focus on playing a consultative sales role on high-value, multi-service, complex deals.
• Lead the full enterprise sales cycle from initial qualification through proposal and pitch organization + facilitation, scoping, negotiation and close.
• Develop deal strategies tailored to executive, multi-stakeholder buying committees within large B2B organizations.
• Contribute to improved win rates, grow average deal size and help scale the agency’s enterprise pipeline year over year.
• Serve as the senior seller for qualified inbound enterprise leads.
• Run advanced discovery to understand prospect challenges, strategic priorities and growth goals.
• Partner with senior service delivery leaders to build thoughtful, outcomes-focused proposals.
• Ensure a seamless, exceptional prospect experience through every stage of the sales journey.
• Collaborate with Growth team Leadership on building an outbound function and identifying necessary resources.
• Oversee the outbound motion targeting B2B companies in our ideal customer profile.
• Collaborate with marketing to launch and optimize outbound campaigns, messaging and account engagement to ensure a consistent flow of high-quality enterprise opportunities.
• Track outbound contribution and continuously refine approach to maximize ROI.
• Strengthen enterprise sales methodology, ensuring consistent execution across discovery, pitch and close phases.
• Facilitate weekly pipeline reviews; maintain accurate forecasting and Salesforce hygiene.
• Identify gaps in sales enablement materials and collaborate with marketing to develop new case studies, capability decks, vertical insights and thought leadership.
• Provide coaching and guidance to services team sellers on best practices for enterprise deal strategy and value-based selling.
• Work closely with Marketing to refine enterprise ICPs, share insights on market trends and influence ABM-focused demand generation initiatives.
• Partner with senior service delivery leaders (VPs and directors) on proposal development, pitch team coordination, and smooth handoff from prospect to client.
• Help shape positioning, messaging, and go-to-market approaches for new or evolving service offerings.
• Represent Walker Sands as a senior ambassador in the enterprise market.
• Support content initiatives and events that elevate the agency’s credibility with C-level B2B buyers.
• Build long-term relationships with PE firms, portfolio companies and senior leaders across industries.

Benefits

• Comprehensive medical, dental, and vision plans, plus mental health resources, pet insurance, fertility benefits, and more.
• Employer-matched 401(k) and access to financial planning services.
• Take time as needed for vacations, mental health, or personal days. Includes 8 paid holidays, half-day summer Fridays, and a week off between Christmas and New Year.
• Mix of in-office and remote work, with tools to stay connected across teams.
• Celebrate five years with a two-week sabbatical and a $2,000 gift.
• Generous paid leave for new parents and caregivers, plus policies for pregnancy loss, adoption challenges, and more.
• Clear career paths, mentorship programs, and learning events to help you grow professionally.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed