Regional Director - Midwest

deepwatch - Chicago, IL

Full-timeEstimated: $140,000 - $190,000 a year
Who We Are
deepwatch is redefining cybersecurity and is one of the fastest growing companies in the U.S. (Top 50 based on last year’s Inc5000). deepwatch serves an impressive list of Fortune 50 and Global 2000 companies as well as numerous mid-sized enterprises. We’ve established strategic partnerships with leading security vendors and serve as a trusted advisor to our customers. Our Core Values drive all aspects of the business and have been paramount to the company’s success and foster our dynamic, entrepreneurial workplace. At deepwatch, your colleagues are some of the most technically astute minds in cybersecurity, who are passionate, knowledgeable, and willing to provide mentorship and guidance at every opportunity.

deepwatch’s next generation Managed Security Services (MSSP) solution is redefining the industry. If you have the passion, work ethic, winning attitude and competitive mindset to be at the forefront of the best entrepreneurial MSSP in the U.S., we want you on our team.

deepwatch Offers

  • Knowledgeable and skilled colleagues seeking collaboration
  • We pay 100% of our employees’ health, dental, life & disability insurance premiums and a generous portion for dependents
  • We provide access to competitive 401k retirement plans upon eligibility
  • Paid Time Off
  • 10 Company Holidays
  • Most positions allow for some amount of telework and flextime, enabling our employees to manage work & life
  • All employees enjoy a generous mobile phone and home internet allowance
  • Apple products
  • Robust referral bonus program
  • Career paths
  • Training & Development opportunities
Regional Director

deepwatch’s Managed Security Service business unit is seeking a high-energy, experienced Regional Director. This individual will play a key role in driving our continued growth nationally. The Regional Director will report to the VP, Sales and will be responsible for working closely with deepwatch’s national sales organization to drive the sale of our MSS Services to CISOs at large enterprise customers.

The Regional Director will work closely with our sales and executive team as well as with our national partner sales team. The ideal candidate will thrive in a fast-paced, entrepreneurial startup environment. You will be passionate about selling and helping advance innovative solutions and technologies to CEOs, CISOs, CIOs, CTOs and other security team members.

We are seeking candidates who are willing to travel weekly to visit existing and prospective customers.


  • Drive sales bookings of Monthly Recurring Revenues through the successful positioning and sale of Managed Security Services on an annual subscription basis
  • Work effectively with national sales teams across regional offices
  • With the support of our industry leading sales representatives, Solutions Architects, and Principal Consultants you will leverage a consultative sales approach to position our Managed Security Service offerings to customer’s needs
  • Execute against the business plan and make quick adjustments both tactically and strategically
  • Ability to manage and control the sales process at every stage through contract signing
  • Attain quarterly results for sales bookings, revenue and gross margin
  • Learn new and emerging technologies and remain current with information security news, techniques, and trends
  • Leverage exceptional communications skills to lead business and technical presentations, demonstrations and conversations with C-level audiences across major accounts and partners
  • Effectively manage multiple opportunities in a methodical and disciplined manner
  • Willingness to travel extensively (often with short notice)
  • Attend industry trade shows and security related conferences in support of activities
  • Set and manage expectations with senior stakeholders and team members
  • Play an active role in driving growth in a winning, team oriented, hyper responsive culture
  • Build relationships with internal sales teams across our regional offices
  • Provide weekly reporting of sales performance and pipeline
  • Research and position deepwatch’s MSS solutions versus competitors
  • Provide input into overall company strategy and product roadmap
  • Work closely with Marketing to design and implement promotions, campaigns and awareness
  • Other duties as assigned by CEO or CTO
To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Required Experience

  • Bachelor’s degree or Master’s degree or equivalent experience
  • 7+ years sales experience in technology software or information security
  • Strong at selling value versus price with proven experience in selling complex solutions and large deals to senior executives
  • Highly motivated and adept exceeding sales bookings targets versus plan and changing behavior as required
  • Excellent communication skills and ability to interact with partners, executives, and customers on a daily basis
  • Fundamental understanding of software, computer, and network architectures
  • Ability to pass a pre-employment background and drug screen in accordance with applicable laws
Preferred Experience

  • Operational and technical experience with Splunk Enterprise and Splunk Enterprise Security
  • Threat intelligence, EDR, VM, Intrusion Detection and Incident Response
  • NIST Cybersecurity Framework
Equal Opportunity Employer
deepwatch is an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, age, disability status, marital status, sexual orientation, gender identity, genetic information, protected veteran status, or any other characteristic protected by law. In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.