growthroles

Regional VP of Sales, Midwest

Ask Locala Open · verified Sep 24, 2026
Chicago VP Sales Leadership

At a glance

Leadership Sales Leadership role at Ask Locala. Chicago.

In listing

RoleSales Leadership
SeniorityVP
LocationChicago
PostedMay 15, 2026 · 4mo ago
Role brief

Growth Roles summary, based on the employer's posting.

What you'll do

  • Lead, coach, and develop three sellers toward regional revenue goals
  • Find high-growth targets, create win plans, and open strategic conversations with valuable prospects
  • Keep Salesforce pipeline records accurate while forecasting against quarterly and annual targets
  • Build senior relationships across Midwest agencies, brands, clients, partners, and stakeholders
  • Work with marketing, client success, operations, and product on market opportunities and go-to-market strategy

What you bring

  • At least eight years in AdTech or digital advertising, including senior sales or regional management success
  • Chicago residence, plus willingness to travel as needed for roughly fifteen percent of the role
  • Strong command of programmatic, digital media, data, measurement, or advertising technology
  • Deep Midwest media-agency knowledge, especially in Chicago, with established Tier 1 and Tier 2 relationships
  • Evidence of closing complex strategic deals, retaining clients, expanding accounts, and meeting revenue targets

Who this fits

You’ll suit this role if you can operate as a player-coach: selling personally while developing a regional team. It calls for a Chicago-based leader with Midwest agency and brand relationships, senior client access, and comfort presenting to clients and leadership. Travel is expected as needed, at approximately fifteen percent.

From the employer

Locala is hiring a Regional VP of Sales, Midwest. If you are a strategic sales leader who thrives in a fast-moving, entrepreneurial environment and wants to help shape the future of omnichannel advertising, we’d love to hear from you!

Locala is the world’s leading commerce media platform, leveraging consumer insights and location data to increase brand awareness, drive consumers to store, and deliver smarter business outcomes. Our proprietary technology enables local advertising and insights at scale, all while meeting the highest user privacy standards in the industry.

About the Role:

We are looking for a motivated and strategic Regional Vice President of Sales to join our growing AdTech organization. This role is ideal for a high-performing seller ready to take the next step into leadership or someone already leading a regional team. This can include first-time managers who are passionate about coaching, building relationships, and driving revenue growth.

The RVP of Sales will serve as a player/coach, leading by example, managing and developing a team focused on driving new business opportunities, growing strategic accounts, and helping brands and agencies leverage our intelligence platform. This individual should bring a strong hunter mentality, balanced with the ability to foster long-term partnerships and mentor top-performing talent.

You must be based in Chicago for this role.

Your background:

  • Based in Chicago, with the requirement of travel as needed (approx. 15%)

  • 8+ years of experience in Ad Tech/Digital Advertising, with a proven track record in senior sales or regional management

  • Strong understanding of programmatic, digital media, data, measurement, or advertising technology

  • Deep understanding of the media agency landscape in Midwest, particularly in the Chicago market

  • Strong existing relationships with key decision-makers at media agencies and brands (Tier 1 & Tier 2)

  • Demonstrated ability to open doors and initiate strategic conversations with high-value prospects

  • Proven success in closing complex, strategic deals and building long-term client partnerships

  • Proven track record of meeting or exceeding revenue targets

  • Excellent communication, presentation, and relationship-building skills

Key Qualities:

  • Strategic thinker with strong problem-solving skills

  • Resilient and adaptable in a fast-moving and evolving industry

  • Collaborative leader with a team-first mindset with low ego; shares best practices and supports colleagues and team

  • Solution-oriented with a consultative approach to client challenges

  • Strong communicator comfortable presenting to internal leadership and external clients

  • Detail-oriented with strong follow-through and organizational skills

  • Market Curiosity - Stays up to date on industry trends and market perspective that build client credibility. Shares market intelligence to help inform team

Responsibilities

  • Lead, mentor, and develop a team of (3) sellers to exceed revenue goals

  • Identify high growth targets & develop and execute plans to win accounts

  • Report weekly on regional performance, wins, challenges, and growth opportunities to VP of West/Central

  • Forecast revenue accurately and manage sales performance against quarterly and annual targets

  • Salesforce reflects an accurate, well-documented pipeline that doesn't surprise leadership

  • Build and maintain senior-level relationships with clients, partners, and key stakeholders in Midwest market

  • Collaborate cross-functionally with marketing, client success, operations, and product

  • Identify new market opportunities and proactively contribute to overall GTM strategy

  • Participate in client meetings, industry events, and presentations

  • Foster a positive, collaborative, and high-performance team culture

  • Provide market feedback to upper management

  • Perform quarterly business and account reviews

  • Cultivate and expand relationships with key decision-makers

  • Drive client retention and expansion efforts, maximizing revenue from existing accounts

Why Join Us

  • Independently owned and management-run

  • Profitable for multiple consecutive years

  • Proprietary, differentiated technology stack

  • Strong employee tenure and collaborative culture

  • Significant upside and growth opportunity

  • Ability to influence strategy and shape the future of the business

In addition to an engaging company culture, a remote-first work environment and training & development, future Localers can expect a competitive benefits package that includes:

  • Medical, Dental & Vision Insurance - 100% paid for the employee-only, 80% for dependents

  • 401k with Company Match

  • Paid Parental Leave

  • Paid Vacation, Sick Time & Holidays

  • Salary range for this role is $150-175K, with a competitive compensation package

    • Note: Actual compensation will vary depending on a candidate’s location, qualifications, and experience. We review our compensation data regularly to ensure we remain competitive.

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