growthroles

Regional Sales Director

Synack synack.com Open · verified Sep 22, 2026
Remote in the Chicago Metro Area Director Sales Leadership

At a glance

Leadership Sales Leadership role at Synack. Remote, United States · $280,000–$320,000 base.

SalaryStated by Synack
$280,000 – $320,000
Base salary for this role, in USD per year, as published in the posting.
RoleSales Leadership
SeniorityDirector
Locationin the Chicago Metro Area
WorkplaceRemote
Base pay$280,000–$320,000
PostedJun 18, 2026 · 3mo ago
Role brief

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

What you'll do

  • Grow enterprise business in the Chicago territory, prioritizing new customer logos while supporting existing accounts
  • Find and develop relationships across major enterprise accounts, including contacts beyond security teams
  • Lead technical and business discovery, handle objections, and guide executive buyers through complex deals
  • Prepare proposals, bids, statements of work, and RFI or RFP responses for senior prospects and customers
  • Coordinate with internal teams, reseller contacts, and technical integration partners to move opportunities forward

What you bring

  • At least eight years selling SaaS cybersecurity products to enterprise companies, ideally in application security or penetration testing
  • A track record of owning the full sales journey, from finding prospects through closing, with a strong new-business focus
  • The ability to align customer decision-makers, identify unstated needs, and communicate effectively with executives
  • Confidence managing every deal stage independently, including conversations with C-suite stakeholders and objection handling

Who this fits

You'll suit a self-directed enterprise cybersecurity seller who can build a territory, win new logos, and manage complex sales independently. This is a remote individual-contributor role, and you must live in the Chicago Metro Area. The stated on-target earnings range is $280,000 to $320,000, with possible equity and benefits.

From the employer

Synack’s Penetration Testing as a Service platform manages customers’ attack surfaces by discovering new assets, pentesting for critical vulnerabilities and gaining visibility into the root causes of security risks. We are committed to making the world more secure by harnessing a talented, vetted community of security researchers to deliver continuous penetration testing and vulnerability management, with actionable results. Synack's PTaaS platform has uncovered more than 71,000 exploitable vulnerabilities to date, protecting a growing list of Global 2000 customers and U.S. agencies in a FedRAMP Moderate Authorized environment. For more information, please visit www.synack.com.

We are seeking a Regional Sales Director with demonstrated selling experience in cybersecurity to grow the territory for enterprises headquartered in the Chicago Metro Area. This role will require continued pipeline expansion with emphasis on new logos and nurturing of existing clients.

You will navigate complex accounts, build strong relationships in and outside of the security organization, generate and deliver winning proposals, contract bids, statements of work, and RFI/RFP responses. Reporting to the Regional Vice President of Sales, this is an individual contributor role requiring a highly motivated self-starter responsible for achieving sales quotas and goals in line with the overall sales strategies for the regional territory. This is a remote position and qualified candidates must be located in the Chicago Metro Area. Please note, this is an individual contributor role.

Sounds interesting? Keep reading...

Here’s what you'll do

  • Build and expand our business with an emphasis on new logos
  • Prospect and build relationships in key enterprise accounts
  • Facilitate business and technical discovery conversations and overcome objections with technical stakeholders
  • Create and deliver proposals, contract bids and statements of work to C-level prospects and customers
  • Work cross functionally with associated internal teams that help progress the selling effort

Here’s what you’ll need

  • 8+ years of sales experience selling SaaS cybersecurity solutions to enterprise companies; preferably cybersecurity, application security or penetration testing solutions
  • History demonstrating command and leadership of the entire sales lifecycle with a hunter mentality
  • Demonstrated ability to align customer stakeholders, uncover implicit needs and communicate clearly in executive conversations and presentations
  • Entrepreneurial approach to developing your territory with mastery of the entire sales process from prospecting leads to close
  • Confident and successful driving a deal through all stages of the deal cycle independently
  • Comfortable speaking to the C-suite and the ability to overcome objections
  • Relationships and experience working with reseller and technical integration partners

Ready to join us?

Synack is committed to embracing diversity. Our people are our strength. Each addition to our team is an opportunity to grow and diversify our ideas, experiences, and viewpoints. Synack strives to be inclusive of all people.

As a candidate, Synack cares about your privacy. Please view our candidate privacy policy.

This position has responsibility to ensure Synack’s security and privacy posture is maintained.

$280,000 - $320,000

The range listed represents a reasonable estimate of the on target earnings for this role based on national salary averages. Salary offered to a successful candidate is determined by a combination of factors including location, level, relevant experience, role related education and skills. The compensation package for this position may also include equity and benefits.

For more details about our benefits, please see our benefits overview. Then for the Employer code, enter: synack

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