Director of Information Security

Operations Indianapolis, Indiana United States


Please Note: For the health and safety of our employees, Lessonly’s physical office is currently closed due to the COVID-19 Pandemic. All of our employees are working remotely and we are re-evaluating the opening date of our office on an ongoing basis.

Director of Information Security

Lessonly is seeking a Director of Information Security to join our team. In this role, you’ll work cross-functionally to maintain and enhance our information security program. Primary focuses of this role include:

Data security program management

  • Maintain our cyber risk management program and roadmap, in partnership with Lessonly’s Executive team. 
  • Serve as lead on any data security events and advise Lessonly’s Executive team on appropriate actions.
  • Lead annual SOC 2 Type 2 audit and maintain related controls.
  • Lead other information security-related programs that include, but are not limited to internal/external penetration testing, security awareness training for employees, and scanning.
  • Maintain programs for app intrusion, incident response, and breach management.
  • Partner with our Engineering team to ensure our application environment is configured to ensure security of customer data.

Support security-related requests from customers

  • Interface directly with information security personnel at customers/prospects to address requests about Lessonly’s data security program.
  • Respond to security questionnaires.
  • Ensure adherence to data security commitments Lessonly makes to customers.


  • Mentor teammates on data security best practices. 
  • Maintain all security-related policies/standards.
  • Design and implement vendor risk/security assessment process for vendors.
  • Ensure compliance with rapidly changing laws and applicable regulations.
  • Maintain the “culture of trust” at Lessonly.  This means that security is top-of-mind for all employees regardless of role.


  • 5+ years of experience leading information security programs in the software industry.
  • Extensive experience administering a SOC 2 audit process and related controls.
  • Flexibility and eagerness to work in a fast-paced environment and meet tight deadlines.

Reports to: Chief Financial Officer 

About Lessonly

Lessonly builds modern training software that helps more than 1,000 sales and support teams do better work. With Lessonly, companies and managers quickly transform knowledge into shareable lessons and resources, engage employees through interactive feedback loops, accelerate rep and team performance, and measure the impact of better learning across their organizations. 

Lessonly Benefits

  • Health Insurance - Medical, vision, dental, and life plans available.
  • Disability Insurance - Short-term and long-term coverage.
  • Paid Parental Leave - Because time with your new baby llama is important.
  • Unlimited PTO - We believe in making time for life, so we like to keep this benefit simple. 
  • 401k Plan - Save and prepare for the future with us.
  • Equity - When we win as a team, you should win, too. 
  • Flexibility - What works best for you, works for us—whether that means you’re in the office, at a coffee shop, or at your kitchen table. We have llamas working in Indy and across the U.S. We also provide everyone with a tech stipend to keep their tech rocking and rolling smoothly.
  • Work Happier - Our community is one of recognition and fun. From company-wide shoutouts to dogs in the office to our vibrant Slack workspace, we’re constantly collaborating and celebrating together. 
  • Make Indy Brighter - Every year, we select four organizations that serve kids in Indianapolis and dedicate our time, money, and talent to them. Making time to volunteer and give back to our community matters.
  • Professional Development - We learn from experts, community leaders, and each other constantly. From Mass Classes and workshops to company events and daily conversations, we’re always growing.
  • Accessibility - We’re conveniently located in the Monon16 neighborhood, right by the Monon Trail and the Red Line if you prefer to run, walk, bike, or bus to work. 
  • Self-Care - We have in-house yoga, ping-pong, Peloton bikes, a meditation room, a library for silent work, a mother’s room, wellness groups, and more because we’re humans first and llamas second.


Lessonly is an Equal Opportunity Employer, we do not discriminate against any protected class including, race, color, religion, sex, national origin, sexual orientation, gender identity, genetic information, disability or protected veteran status. Lessonly will provide reasonable accommodation to qualified individuals with disabilities. Please contact [email protected] if you require a reasonable accommodation to apply for a job.