Allstate
Strategic Planning Expert (Chicago, IL)
Key aspects of the role:
- Drive sales growth by engaging with interested prospective customers- all while working remote
- No cold calling— Connect through inbound calls and proactive outbound calls with active insurance shoppers
- Enjoy competitive compensation with a base salary + uncapped performance-based incentives
- Sell reputable products from Allstate and our family of brands
Role overview
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.
Job Description
The Cybersecurity Strategic Planning Expert helps Allstate Cybersecurity & Controls (ACC) leaders turn complex cybersecurity risks, strategies, performance information, and technical initiatives into clear decisions, aligned action, and measurable outcomes. As part of the ACC Strategy team, this role develops compelling narratives and executive-ready communications for the Chief Information Security Officer (CISO), ACC leadership, senior executives, the Board, and the Audit Committee. Operating as a trusted advisor in an evolving and often ambiguous environment, the role brings structure to complex questions, synthesizes technical and business perspectives, and frames priorities, trade-offs, risks, and recommendations in concise, non-technical language. Success is reflected in stronger executive decision-making, consistent strategic narratives, greater visibility into cybersecurity posture and outcomes, clear accountability, and coordinated progress on the highest-priority risks.
Key Responsibilities
- Develop clear, compelling cybersecurity narratives for the CISO, senior executives, Board, and Audit Committee.
- Translate complex cybersecurity risks, strategies, metrics, and technical initiatives into concise, non-technical, decision-ready communications.
- Create executive-level presentations and communications, including briefings, talking points, strategic reports, leadership updates, and Board materials.
- Support the development and governance of the Allstate Cybersecurity & Controls (ACC) strategy, ensuring alignment with enterprise priorities, business strategy, and the evolving cybersecurity risk environment.
- Monitor cybersecurity threats, regulatory developments, technology trends, and business changes to identify strategic implications and emerging priorities.
- Coordinate cross-functional strategic governance, including key commitments, portfolio outcomes, dependencies, risks, metrics, and leadership decisions.
- Measure and communicate strategic progress and cybersecurity outcomes through meaningful metrics, trends, gaps, and indicators of risk reduction.
- Analyze complex and ambiguous business and cybersecurity challenges, combining quantitative and qualitative information to develop practical recommendations.
- Frame strategic options, trade-offs, and recommendations and facilitate leadership discussions around prioritization, sequencing, and risk-informed decision-making.
- Build alignment across cybersecurity and enterprise partners, including Technology, Enterprise Risk, Legal, Compliance, Internal Audit, and Communications, while strengthening governance practices and team standards.
Required Education and Experience
- 4+ years of experience in strategy, executive communications, strategic planning, management consulting, business analysis, portfolio governance, risk, technology, financial services, or related roles.
- Demonstrated experience developing executive presentations, strategic narratives, briefing materials, or Board-facing content and synthesizing complex technical and business information into clear insights and recommendations.
- Experience supporting strategy development, governance, metrics, portfolio reporting, facilitation, cross-functional decision-making, or senior executive communications.
- Experience in cybersecurity, technology, risk, consulting, financial services, insurance, or another complex regulated environment preferred.
- Must be willing and able to travel into our Chicago, Illinois office on an as needed basis.
#LI-JA2
Skills
Business Strategies, Enterprise Strategies, Process Improvements, Strategic Objectives, Strategic Planning, Strategic Thinking, Strategy Development
Compensation
Compensation offered for this role is 100,000.00 – 170,500.00 annually and is based on experience and qualifications.
The candidate(s) offered this position will be required to submit to a background investigation.
Joining our team isn’t just a job — it’s an opportunity. One that takes your skills and pushes them to the next level. One that encourages you to challenge the status quo. One where you can shape the future of protection while supporting causes that mean the most to you. Joining our team means being part of something bigger – a winning team making a meaningful impact.
Allstate generally does not sponsor individuals for employment-based visas for this position.
Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.
For jobs in San Francisco, please click “here” for information regarding the San Francisco Fair Chance Ordinance.
For jobs in Los Angeles, please click “here” for information regarding the Los Angeles Fair Chance Initiative for Hiring Ordinance.
To view the “EEO Know Your Rights” poster click “here”. This poster provides information concerning the laws and procedures for filing complaints of violations of the laws with the Office of Federal Contract Compliance Programs.
To view the FMLA poster, click “here”. This poster summarizing the major provisions of the Family and Medical Leave Act (FMLA) and telling employees how to file a complaint.
It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.
Allstate provides a comprehensive technology setup, including a laptop, monitors, headset, keyboard, and mouse. Employees eligible to work from home also receive a monthly connectivity reimbursement to help offset internet costs.
When working from home, you must have a dedicated, private workspace free from distractions, along with appropriate desk and seating. Reliable internet is required, with minimum speeds of 50 MB download and 5 MB upload.
To help create a more personal and engaging experience, we ask that you join with your camera on if your interview is virtual. Please also have a Valid Photo Identification available at the start of your interview. If you require any accommodations or have questions ahead of your interview please reach out to your recruiter.
Note: Internal candidates are only asked to join on video; a Valid Photo Identification is not needed for the interview.
Keys to Success
At Allstate, it’s all about teamwork, flexibility, and thinking ahead. We all contribute to the bigger picture, combining unique ideas to design innovative, more affordable protection solutions for customers.
We look for candidates with these skills to help us achieve that goal:
Learning agility
Quickly adapt to new situations, continually build new skills, experiment, and embrace new ways of doing things
Customer centricity
Deliver exceptional experience with a customer-first mindset and human-centered design
Digital literacy
Discover and apply emerging digital technology tools, data and insights.
Results-oriented
Start with measurable outcomes and drive results with speed
Inclusive leadership
Integrate diverse viewpoints into decision-making processes to enhance creativity and innovation
Together, we’re all working toward Our Shared Purpose, using our strengths to make a real difference for our people, our customers, our company, and the world around us.
Working in Sales
What We Do:
As an expert on our products and services, you can give customers personalized attention and innovative solutions to make their lives easier.
How We Support You:
Starting day one, you’ll have access to resources and incentives to keep you feeling challenged and excited about your careers.
Make An Impact:
As a member of our sales team, you’ll bring a sense of ease and support to customers looking for a better understanding of their protection options. Whether in the field or talking to customers over the phone, you’ll continue to build trust in who we are and what we do.
Working together
You’re in Good Hands® is more than a promise we make to our customers. It’s a promise we make to our employees, too.
We want you to love where you work. That starts with the freedom to be yourself. Our workplace flexibility and focus on individuality means everyone is seen, heard and respected.
When you join us, you’ll have the opportunity to push your skills to the next level with access to development programs to support your career aspirations – whatever that means for you. Because as you learn and grow, so do we.
Working here also means getting the chance to make a real impact in your community. We have been driving change for over 90 years, but the mark we leave on the world can be even greater when we work together.
Role overview
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.
Job Description
The Cybersecurity Strategic Planning Expert helps Allstate Cybersecurity & Controls (ACC) leaders turn complex cybersecurity risks, strategies, performance information, and technical initiatives into clear decisions, aligned action, and measurable outcomes. As part of the ACC Strategy team, this role develops compelling narratives and executive-ready communications for the Chief Information Security Officer (CISO), ACC leadership, senior executives, the Board, and the Audit Committee. Operating as a trusted advisor in an evolving and often ambiguous environment, the role brings structure to complex questions, synthesizes technical and business perspectives, and frames priorities, trade-offs, risks, and recommendations in concise, non-technical language. Success is reflected in stronger executive decision-making, consistent strategic narratives, greater visibility into cybersecurity posture and outcomes, clear accountability, and coordinated progress on the highest-priority risks.
Key Responsibilities
- Develop clear, compelling cybersecurity narratives for the CISO, senior executives, Board, and Audit Committee.
- Translate complex cybersecurity risks, strategies, metrics, and technical initiatives into concise, non-technical, decision-ready communications.
- Create executive-level presentations and communications, including briefings, talking points, strategic reports, leadership updates, and Board materials.
- Support the development and governance of the Allstate Cybersecurity & Controls (ACC) strategy, ensuring alignment with enterprise priorities, business strategy, and the evolving cybersecurity risk environment.
- Monitor cybersecurity threats, regulatory developments, technology trends, and business changes to identify strategic implications and emerging priorities.
- Coordinate cross-functional strategic governance, including key commitments, portfolio outcomes, dependencies, risks, metrics, and leadership decisions.
- Measure and communicate strategic progress and cybersecurity outcomes through meaningful metrics, trends, gaps, and indicators of risk reduction.
- Analyze complex and ambiguous business and cybersecurity challenges, combining quantitative and qualitative information to develop practical recommendations.
- Frame strategic options, trade-offs, and recommendations and facilitate leadership discussions around prioritization, sequencing, and risk-informed decision-making.
- Build alignment across cybersecurity and enterprise partners, including Technology, Enterprise Risk, Legal, Compliance, Internal Audit, and Communications, while strengthening governance practices and team standards.
Required Education and Experience
- 4+ years of experience in strategy, executive communications, strategic planning, management consulting, business analysis, portfolio governance, risk, technology, financial services, or related roles.
- Demonstrated experience developing executive presentations, strategic narratives, briefing materials, or Board-facing content and synthesizing complex technical and business information into clear insights and recommendations.
- Experience supporting strategy development, governance, metrics, portfolio reporting, facilitation, cross-functional decision-making, or senior executive communications.
- Experience in cybersecurity, technology, risk, consulting, financial services, insurance, or another complex regulated environment preferred.
- Must be willing and able to travel into our Chicago, Illinois office on an as needed basis.
#LI-JA2
Skills
Business Strategies, Enterprise Strategies, Process Improvements, Strategic Objectives, Strategic Planning, Strategic Thinking, Strategy Development
Compensation
Compensation offered for this role is 100,000.00 – 170,500.00 annually and is based on experience and qualifications.
The candidate(s) offered this position will be required to submit to a background investigation.
Joining our team isn’t just a job — it’s an opportunity. One that takes your skills and pushes them to the next level. One that encourages you to challenge the status quo. One where you can shape the future of protection while supporting causes that mean the most to you. Joining our team means being part of something bigger – a winning team making a meaningful impact.
Allstate generally does not sponsor individuals for employment-based visas for this position.
Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.
For jobs in San Francisco, please click “here” for information regarding the San Francisco Fair Chance Ordinance.
For jobs in Los Angeles, please click “here” for information regarding the Los Angeles Fair Chance Initiative for Hiring Ordinance.
To view the “EEO Know Your Rights” poster click “here”. This poster provides information concerning the laws and procedures for filing complaints of violations of the laws with the Office of Federal Contract Compliance Programs.
To view the FMLA poster, click “here”. This poster summarizing the major provisions of the Family and Medical Leave Act (FMLA) and telling employees how to file a complaint.
It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.
Allstate provides a comprehensive technology setup, including a laptop, monitors, headset, keyboard, and mouse. Employees eligible to work from home also receive a monthly connectivity reimbursement to help offset internet costs.
When working from home, you must have a dedicated, private workspace free from distractions, along with appropriate desk and seating. Reliable internet is required, with minimum speeds of 50 MB download and 5 MB upload.
To help create a more personal and engaging experience, we ask that you join with your camera on if your interview is virtual. Please also have a Valid Photo Identification available at the start of your interview. If you require any accommodations or have questions ahead of your interview please reach out to your recruiter.
Note: Internal candidates are only asked to join on video; a Valid Photo Identification is not needed for the interview.
Keys to Success
At Allstate, it’s all about teamwork, flexibility, and thinking ahead. We all contribute to the bigger picture, combining unique ideas to design innovative, more affordable protection solutions for customers.
We look for candidates with these skills to help us achieve that goal:
Learning agility
Quickly adapt to new situations, continually build new skills, experiment, and embrace new ways of doing things
Customer centricity
Deliver exceptional experience with a customer-first mindset and human-centered design
Digital literacy
Discover and apply emerging digital technology tools, data and insights.
Results-oriented
Start with measurable outcomes and drive results with speed
Inclusive leadership
Integrate diverse viewpoints into decision-making processes to enhance creativity and innovation
Together, we’re all working toward Our Shared Purpose, using our strengths to make a real difference for our people, our customers, our company, and the world around us.
Working in Claims
What We Do:
Your ability to quickly and calmly make smart decisions can make a huge difference in how confident customers feel throughout the claims process. And as you support our customers, we’re there to support you.
How We Support You:
We empower your success starting day one. You’ll have access to everything you need to grow professionally while helping our customers get their lives back on track.
Make An Impact:
Helping customers with their claims is about learning their stories, not just processing their paperwork. You can take pride in the fact that you’re providing invaluable guidance and helping to build continued trust in our company.
Working together
You’re in Good Hands® is more than a promise we make to our customers. It’s a promise we make to our employees, too.
We want you to love where you work. That starts with the freedom to be yourself. Our workplace flexibility and focus on individuality means everyone is seen, heard and respected.
When you join us, you’ll have the opportunity to push your skills to the next level with access to development programs to support your career aspirations – whatever that means for you. Because as you learn and grow, so do we.
Working here also means getting the chance to make a real impact in your community. We have been driving change for over 90 years, but the mark we leave on the world can be even greater when we work together.
Role overview
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.
Job Description
The Cybersecurity Strategic Planning Expert helps Allstate Cybersecurity & Controls (ACC) leaders turn complex cybersecurity risks, strategies, performance information, and technical initiatives into clear decisions, aligned action, and measurable outcomes. As part of the ACC Strategy team, this role develops compelling narratives and executive-ready communications for the Chief Information Security Officer (CISO), ACC leadership, senior executives, the Board, and the Audit Committee. Operating as a trusted advisor in an evolving and often ambiguous environment, the role brings structure to complex questions, synthesizes technical and business perspectives, and frames priorities, trade-offs, risks, and recommendations in concise, non-technical language. Success is reflected in stronger executive decision-making, consistent strategic narratives, greater visibility into cybersecurity posture and outcomes, clear accountability, and coordinated progress on the highest-priority risks.
Key Responsibilities
- Develop clear, compelling cybersecurity narratives for the CISO, senior executives, Board, and Audit Committee.
- Translate complex cybersecurity risks, strategies, metrics, and technical initiatives into concise, non-technical, decision-ready communications.
- Create executive-level presentations and communications, including briefings, talking points, strategic reports, leadership updates, and Board materials.
- Support the development and governance of the Allstate Cybersecurity & Controls (ACC) strategy, ensuring alignment with enterprise priorities, business strategy, and the evolving cybersecurity risk environment.
- Monitor cybersecurity threats, regulatory developments, technology trends, and business changes to identify strategic implications and emerging priorities.
- Coordinate cross-functional strategic governance, including key commitments, portfolio outcomes, dependencies, risks, metrics, and leadership decisions.
- Measure and communicate strategic progress and cybersecurity outcomes through meaningful metrics, trends, gaps, and indicators of risk reduction.
- Analyze complex and ambiguous business and cybersecurity challenges, combining quantitative and qualitative information to develop practical recommendations.
- Frame strategic options, trade-offs, and recommendations and facilitate leadership discussions around prioritization, sequencing, and risk-informed decision-making.
- Build alignment across cybersecurity and enterprise partners, including Technology, Enterprise Risk, Legal, Compliance, Internal Audit, and Communications, while strengthening governance practices and team standards.
Required Education and Experience
- 4+ years of experience in strategy, executive communications, strategic planning, management consulting, business analysis, portfolio governance, risk, technology, financial services, or related roles.
- Demonstrated experience developing executive presentations, strategic narratives, briefing materials, or Board-facing content and synthesizing complex technical and business information into clear insights and recommendations.
- Experience supporting strategy development, governance, metrics, portfolio reporting, facilitation, cross-functional decision-making, or senior executive communications.
- Experience in cybersecurity, technology, risk, consulting, financial services, insurance, or another complex regulated environment preferred.
- Must be willing and able to travel into our Chicago, Illinois office on an as needed basis.
#LI-JA2
Skills
Business Strategies, Enterprise Strategies, Process Improvements, Strategic Objectives, Strategic Planning, Strategic Thinking, Strategy Development
Compensation
Compensation offered for this role is 100,000.00 – 170,500.00 annually and is based on experience and qualifications.
The candidate(s) offered this position will be required to submit to a background investigation.
Joining our team isn’t just a job — it’s an opportunity. One that takes your skills and pushes them to the next level. One that encourages you to challenge the status quo. One where you can shape the future of protection while supporting causes that mean the most to you. Joining our team means being part of something bigger – a winning team making a meaningful impact.
Allstate generally does not sponsor individuals for employment-based visas for this position.
Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.
For jobs in San Francisco, please click “here” for information regarding the San Francisco Fair Chance Ordinance.
For jobs in Los Angeles, please click “here” for information regarding the Los Angeles Fair Chance Initiative for Hiring Ordinance.
To view the “EEO Know Your Rights” poster click “here”. This poster provides information concerning the laws and procedures for filing complaints of violations of the laws with the Office of Federal Contract Compliance Programs.
To view the FMLA poster, click “here”. This poster summarizing the major provisions of the Family and Medical Leave Act (FMLA) and telling employees how to file a complaint.
It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.
Allstate provides a comprehensive technology setup, including a laptop, monitors, headset, keyboard, and mouse. Employees eligible to work from home also receive a monthly connectivity reimbursement to help offset internet costs.
When working from home, you must have a dedicated, private workspace free from distractions, along with appropriate desk and seating. Reliable internet is required, with minimum speeds of 50 MB download and 5 MB upload.
To help create a more personal and engaging experience, we ask that you join with your camera on if your interview is virtual. Please also have a Valid Photo Identification available at the start of your interview. If you require any accommodations or have questions ahead of your interview please reach out to your recruiter.
Note: Internal candidates are only asked to join on video; a Valid Photo Identification is not needed for the interview.
Keys to Success
At Allstate, it’s all about teamwork, flexibility, and thinking ahead. We all contribute to the bigger picture, combining unique ideas to design innovative, more affordable protection solutions for customers.
We look for candidates with these skills to help us achieve that goal:
Learning agility
Quickly adapt to new situations, continually build new skills, experiment, and embrace new ways of doing things
Customer centricity
Deliver exceptional experience with a customer-first mindset and human-centered design
Digital literacy
Discover and apply emerging digital technology tools, data and insights.
Results-oriented
Start with measurable outcomes and drive results with speed
Inclusive leadership
Integrate diverse viewpoints into decision-making processes to enhance creativity and innovation
Together, we’re all working toward Our Shared Purpose, using our strengths to make a real difference for our people, our customers, our company, and the world around us.
Working together
You’re in Good Hands® is more than a promise we make to our customers. It’s a promise we make to our employees, too.
We want you to love where you work. That starts with the freedom to be yourself. Our workplace flexibility and focus on individuality means everyone is seen, heard and respected.
When you join us, you’ll have the opportunity to push your skills to the next level with access to development programs to support your career aspirations – whatever that means for you. Because as you learn and grow, so do we.
Working here also means getting the chance to make a real impact in your community. We have been driving change for over 90 years, but the mark we leave on the world can be even greater when we work together.
Benefits
Experience the benefits that make Allstate a great place to work.
*Benefits vary based on position.
Health
- Medical, dental and vision coverage
- HSAs and FSAs
- Wellbeing programs
- Free therapy sessions
Retirement
- 401(k) plan
- Pension plan
- Free financial counseling
Work-life balance
- Paid time off
- Work flexibility
Career development
- Talent shares
- Tuition reimbursement
- Learning opportunities
For a full description of Allstate’s benefits visit our benefits page
Start making a difference
Realize your full potential by doing
work that matters.
Grow your career in meaningful ways.
We want to make sure you have every opportunity to grow, explore new horizons and follow your passion in a meaningful career. It’s an exciting time to join Allstate. Help us shape the future.
Ryan / 8 years with Allstate
Business Architect Lead Consultant
June 2025 – Present
Anthony / 11 years with Allstate
New Agent Leader- EA Channel
February 2026 – Present
Michael / 25 years with Allstate
Property Delivery Director
2023 – Present/Remote
Bree / 11 years with Allstate
Unrepresented Bodily Injury Adjuster
December 2022 – Present
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