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This position has closed. Allstate removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Technology Strategy Leader

Allstate · IL · Full time

Posted Aug 5, 2026 · We last checked this listing on Oct 4, 2026

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a broad strategic initiative you led. How did you get senior leaders to commit to it?

What they are checking: Whether they can build executive sponsorship and carry a strategy through to execution, not just a deck.

How do you develop strategists on your team who are strong analysts but weak at influencing executives?

What they are checking: Whether they coach people on presence and storytelling, not just on analysis quality.

Tell me about a time a strategy you set turned out to be wrong. How did you recognize it and respond?

What they are checking: Whether they revisit decisions when evidence changes rather than defending a past call to save face.

Tell me about a time you turned a long-term vision into a near-term plan people could start on Monday.

What they are checking: Whether they can connect big direction to concrete first steps so strategy actually gets executed.

What would you do

How do you keep your team's perspective independent while still being a trusted partner to the business units?

What they are checking: Whether they can balance candor with relationships, which is the core of an advisory strategy role.

Two senior leaders want your team's capacity for competing priorities. How do you decide?

What they are checking: Whether they prioritize on enterprise value and communicate the trade-off openly to both leaders.

How do you build a view on where the technology market is going without getting captured by vendors?

What they are checking: Whether they use multiple sources, including analysts, peers and experiments, to form an independent view.

About the work

How would you set the agenda for a technology strategy team so its work actually shapes enterprise decisions?

What they are checking: Whether they know how to pick the few questions that matter most to senior leaders and focus the team there.

Walk me through how you'd assess the impact of generative AI on Allstate's operating model.

What they are checking: Whether they can frame a broad topic into specific opportunities, risks and investments leaders can act on.

How would you measure the success of a technology strategy team?

What they are checking: Whether they tie the team's worth to decisions influenced and outcomes achieved, not to reports produced.

Practice this interview out loud.

Offer builds a real interview for this exact role at Allstate from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Allstate.

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 Our technology strategists evaluate broad technology trends and disruptive innovations and then interpret the implications and opportunities for our business. We provide an objective, independent perspective enabling Allstate to realize the full potential of technology resources, investments and assets. As advisory partners, we bring together the right voices and thought leadership to make informed decisions and set the strategic direction for how Allstate can leverage technology to create competitive advantage. The Technology Strategy Senior Manager is responsible for leading the design, delivery and execution of broad strategic initiatives to deliver on department and broader Enterprise goals. Additionally, the Technology Strategy Senior Manager will partner with senior leaders from across the enterprise to develop cutting-edge technology strategies that enable Allstate to achieve near and long-term goals. Key Responsibilities • Recommends and implements change across multiple organizations in alignment with enterprise change initiatives; uses personal influence to enlist employees and peers in implementing change • Models and creates an environment of accountability within the team, and for peer groups and senior leaders by setting clear objectives in support of strategic business outcomes • Leads team in achieving significant, complex assignments by creating structure and leveraging processes that enable oversight of delivery while allowing employees freedom of action • Leverages in-depth business knowledge to convert thinking of others and/or gains acceptance of complex ideas where difficult (but necessary) to achieve goals and objectives • Establishes a vision, direction, and specific objectives for multiple organizational areas and assists in integrating that vision across multiple areas • Applies knowledge to diverse and complex situations, where alternatives are numerous, to drive business solutions on behalf of the organization • Communicates the technology strategy to the organization so they understand their roles, are motivated to achieve established goals and have line of the sight between their work and Allstate strategies • Responsible for implementation of our enterprise technology strategy, including high-level planning of work and resources • Acting as a thought leader by developing complex ideas that have long-term, strategic impact and align with broader Enterprise strategies Experience • 10 or more years of experience (Preferred) Supervisory Responsibilities • This job has supervisory duties. *This is a hybrid role that will require at least 1 day a week in the office (office locations: Chicago & Northbrook) #LI-JK1 Skills Business Strategies, Employee Supervision, Enterprise Strategies, Process Improvements, Strategic Direction, Strategic Initiative, Strategic Thinking, Strategy Development, Technology Strategies Compensation Compensation offered for this role is 134,000.00 - 209,750.00 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.