Director of Information Security at SilkRoad Technology (Chicago, IL)

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Job Description

SilkRoad Technology is the world's leader in strategic onboarding for global workforce readiness and transformation. We help organizations prepare their people for change by designing intentional, personalized journeys to increase retention and maximize agility throughout their careers. SilkRoad combines our leading strategic onboarding capabilities with world-class consulting services to deliver highly scalable, personalized experiences that engage employees and drive long-term business performance such as productivity, profitability, growth and agility.

Our Information Security team is seeking a Director of Information Security to be an integral part of the team responsible for ensuring the security of SilkRoad's data as well as our customer's data. This role is responsible for determining enterprise information security policy and strategy and oversees the development, implementation, and enforcement of information security standards and procedures.

Your contributions to SilkRoad will include: 

  • Leading, sustaining, and developing experienced teams accountable for information policy, compliance, standards and controls, policy and risk governance, information and technology risk assessment, client privacy, disaster recovery, cyber-defense, incident response, and identity and access management.
  • Coordinating the delivery of security audits, vulnerability assessments, and penetration tests.
  • Overseeing all Information Security team to manage ongoing security initiatives, assessments and audits.
  • Providing information security expertise to the organization by recommending information security initiatives, which mitigate risks, strengthen defenses, and reduce vulnerabilities.
  • Facilitating a metrics and reporting framework to measure the efficiency and effectiveness of the security program.
  • Leading programs and processes to monitor the emergence of new threats and vulnerabilities, assessing impacts and driving responses as appropriate.
  • Reviewing investigations after breaches or incidents, including impact analysis and recommendation for avoiding similar vulnerabilities.
  • Reviewing third party vendors and contracts to ensure appropriate controls are in place and working effectively.
  • Enhancing the competitive position of the organization by supporting and implementing new security and compliance-related products and services.
  • Leading and facilitating information security governance topics, status and advice, including active involvement of and/or leading committees.
  • Cultivating and building collaborative working relationships with a broad range of enterprise stakeholders.
  • Serving as the corporate focal point for security incident response planning, execution, and awareness.
  • Briefing the executive team on status and risks, including taking the role of champion for the overall strategy and necessary budget.
  • Acting as the liaison with external agencies, such as regulators, industry groups, and law enforcement and other as necessary.
  • Understanding current and proposed legal and regulatory data privacy requirements that apply to the organization or its customers such as GDPR, CCPA, foreign cybersecurity regulations, the HIPAA security rule, and various other federal/state notification laws.
  • Representing organizational risk, provide thought leadership in industry and cybersecurity forums, and participate in relevant seminars, forums and committees.
  • Building and enhancing business relationships between our clients and the technical teams of SilkRoad Technology.
  • Leveraging executive level expertise to provide strategic security advice as a trusted security advisor to existing and prospect clientele.
  • Partnering with Sales and Marketing to meet and exceed services revenue quotas through business development activities.
  • Identifying pre-engagement requirements (goals, budgeting, timing, etc.) and assist with the request for proposal creation.
  • Liaising between the Sales and Service delivery organizations within SilkRoad Technology's Security
  • Assisting sales in understanding CISO personas, current industry and market issues/trends and assist in positioning SilkRoad Technology's security solutions to security executives.
  • Providing billable executive sponsorship and delivery of client-facing projects.
  • Being an industry spokesperson in front of both small and larger audiences (such as roundtable events or conferences) and contribute to thought leadership related to practice domain.
Required Skills
  • Expertise knowledge of current and emerging information technology industry trends and directions including common information security management frameworks, such as GDPR, CCPA, FISMA, SOC, NIST 800-53 & CSF, FIPS, HIPPA, HITRUST, ISO/IEC 27001, ITIL, CSA CAIQ, and COBIT.
  • Exceptional leadership, managerial and administrative skills.
  • Ability to work collaboratively across interdisciplinary teams and manage relationships across multiple areas of the business including Professional Services, Sales, Datacenter Operations and other executive stakeholders.
  • Ability to effectively lead change and motivate cross-functional, interdisciplinary teams to achieve tactical and strategic goals.
  • Sound judgment and ability to effectively balance information risk controls with business productivity and growth.
  • Ability to communicate technical information to diverse audiences that include senior management including current and emerging digital security trends and directions.
  • Demonstrated project management skills and ability to track and report progress against established milestones, metrics and deliverables.
  • Excellent verbal and written communication skills as well as strong analytical and problem-solving skills and operate with minimal supervision.
  • Excellent written communication skills, demonstrating the ability to write with purpose, clarity, and accuracy to both technical and non-technical audiences. 
  • Ability to pass extensive background check, and ongoing background checks.
  • Proficient with computer software and MS Office applications, including Word, PowerPoint and Excel.
Required Experience
  • Master's degree in Computer Science, Information Systems, a related field, or equivalent work experience (15 Years+), is required.
  • Minimum of 10 years of IT Security experience.
  • Expertise knowledge of current and emerging information technology industry trends and directions including common information security management frameworks, such as GDPR, CCPA, FISMA, SOC, NIST 800-53 & CSF, FIPS, HIPPA, HITRUST, ISO/IEC 27001, ITIL, CSA CAIQ, and COBIT.
  • At least two of the leading industry certifications such as: C|CISO, CISSP, CISM, and/or CRISC.
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Technology we use

  • Engineering
  • Sales & Marketing
    • C#Languages
    • SqlLanguages
    • SalesforceCRM


We're located at Wacker & Monroe on the Chicago River, steps away from Union Station. The plaza is a great place to enjoy summer sun and food trucks!

An Insider's view of SilkRoad Technology

What are some social events your company does?

We hold social events in the office often at SilkRoad. We have an awesome culture here, so we often have social events to celebrate birthdays, weddings, baby showers, etc. of employees in our Chicago office. We also always have social events when remote employees are in the Chicago office. For example, the other week we had a “game day” at the end.


Manager, Client Renewals

How do you collaborate with other teams in the company?

My role is to actively work with client company executive sponsors and their subject matter experts and to also play a unique role internally within SilkRoad. I collaborate internally with marketing, sales, services, product management & development to bring forth the client’s voice, industry knowledge/trends, best-practices, & thought leadership.


Sr. Director, Strategy & Transformation

How does the company support your career growth?

My manager creates opportunities that align with my goals so I can work on projects that excite me. SilkRoad also invests in the development of all employees by having a resource focused on internal training. We embrace the "commit to your craft" motto by identifying learning opportunities and communicating them through an internal resource hub.


Learning and Development Program Manager

What are SilkRoad Technology Perks + Benefits

SilkRoad Technology Benefits Overview

We complement an environment that fosters success and fun, with a full range of benefits and perks to meet the needs of you and your family. SilkRoad aims to provide peace of mind when it comes to employee's health and financial well-being. We offer a wide range of benefits including health and life insurance, 401(k) plan with company match, volunteer program, and expanded maternity and paternity leave. The perk that transcends the rest is our flexible, work happy environment! SilkRoadies enjoy generous paid time off, flexible work options, and dress for your day freedom.

Volunteer in local community
Paid day off to volunteer and office-based volunteer activities.
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Highly diverse management team
Diversity manifesto
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Onsite Gym
Team workouts
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Employee Stock Purchase Plan
Child Care & Parental Leave Benefits
Generous Parental Leave
We provide 12 weeks of paid maternity/paternity leave and an additional 4 weeks of unpaid leave, for a total of 16 weeks of parental leave.
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Return-to-work program post parental leave
Company sponsored family events
Vacation & Time Off Benefits
Generous PTO
Flexible Time Off - SilkRoadies love the Flexible PTO policy. Our flexible paid time off benefit can be used for vacation, personal / family illness, or personal reasons.
Paid Volunteer Time
Our Volunteer Time Off program provides employees 8 hours per year of paid time off to volunteer.
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
SilkRoad offers commuter spending accounts
Company Outings
Game Room
Stocked Kitchen
Some Meals Provided
Occasional office lunches are provided.
Happy Hours
Recreational Clubs
Fitness Subsidies
Professional Development Benefits
Lunch and learns
SilkRoad hosts lunch and learn meetings throughout the year.
Cross functional training encouraged
Promote from within
Time allotted for learning
Paid industry certifications

Additional Perks + Benefits

SilkRoad realizes the importance of a healthy work-life balance. Our generous PTO and flexible work environment support this balance. For most positions, you control where and how the work gets done. Of course some jobs require more structure, particularly those that directly interface with our customers, but our overall philosophy is that you control your work dynamics and the results are what matter most.

We embrace a people-first culture and have built an environment where employees are valued, and their voices heard. We continually evaluate our benefits programs to ensure they meet the needs of our employees.

Happy, engaged employees mean happy clients!

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