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Support the CFO and SVP of Finance through complex calendar, travel, meeting, presentation, communication, and administrative management. Coordinate priorities, action items, executive and board materials, stakeholder communications, and confidential financial information. The role requires proactive judgment, strong organization, discretion, and the ability to manage competing priorities while improving operational processes and executive effectiveness.
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Handle inbound calls and warm leads, assess customers’ insurance needs, recommend Property and Casualty products and coverages, and convert prospects into policyholders. The role includes paid remote training and licensing, customer consultation, sales closing, and adherence to scheduled shifts. Representatives must maintain a professional home workspace with reliable wired high-speed internet and remain in their resident state for at least one year.
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Attentive® is the AI-powered mobile marketing platform transforming the way brands personalize consumer engagement. Attentive enables marketers to craft tailored journeys for every subscriber, driving higher recurring revenue and maximizing campaign performance. Activating real-time data from multiple channels and advanced AI, the platform personalizes content, tone, and timing to deliver 1:1 messages that truly resonate.
With a top-rated customer success team recognized on G2, Attentive partners with marketers to provide strategic guidance and optimize SMS and email campaigns. Trusted by leading global brands like Neiman Marcus, Samsung, Wayfair, and Dyson, Attentive ensures enterprise-grade compliance and deliverability, supporting trillions of interactions across more than 70 industries. To learn more or request a demo, visit www.attentive.com or follow us on LinkedIn, X (formerly Twitter), or Instagram.
Attentive’s growth has been recognized by Deloitte’s Fast 500, Linkedin’s Top Startups and Forbes Cloud 100 all thanks to the hard work from our global employees!
About the Role
Attentive is looking for an exceptional Executive Assistant to partner with our CFO. This is more than a calendar and travel role. We’re looking for a trusted operator who thrives in a fast-paced environment, knows how to anticipate needs, and can seamlessly toggle between strategic support and detailed execution.
The CFO at Attentive is leading strategic finance initiatives, supporting a global team, and helping to steer the company through its next phase of growth. This role is a rare opportunity to sit at the intersection of product, GTM, and investor conversations at a category-defining company while ensuring the CFO and the finance team can operate at full altitude.
As the right hand to the CFO, you’ll gain exposure to executive decision-making at a company redefining personalized marketing. If you're energized by building structure, love keeping high-level leaders organized and efficient, and want to make an impact at scale, we want to hear from you.
What You’ll Accomplish
- Be a force multiplier for the CFO. Manage scheduling, prep, follow-ups, and internal and external comms to ensure time is spent on the highest-impact priorities
- Drive operational excellence. Organize board meetings, investor interactions, leadership offsites, and financial planning sessions
- Serve as a trusted liaison. Partner with cross-functional executives, internal teams, board members, and external stakeholders with poise and discretion
- Stay steps ahead. Anticipate roadblocks, flag key deadlines, and ensure the CFO is informed and prepared for every conversation
- Keep the engine running. Coordinate travel, expenses, document prep, and ongoing projects with precision and speed
Your Expertise
- 3+ years of experience supporting C-level executives, ideally CFOs in tech or high-growth environments
- Strong judgment, high EQ, and a bias for action
- Comfortable working in ambiguity and fast-moving situations. You don’t wait to be told what to do
- Exceptional written and verbal communication skills. Clear, concise, and executive-ready
- Confidentiality is second nature to you
- Proficient with Google Workspace, Slack, and project management tools
- Location Requirement: Must be based in Pacific or Central Time Zones
You'll get competitive perks and benefits, from health & wellness to equity, to help you bring your best self to work.
For US based applicants:
- The US base salary range for this full-time position is $145,000 - $160,000 annually + equity + benefits
- Equity is a substantial part of the total compensation package
- Our salary ranges are determined by role, level and location
#LI-AL1 #LI-DNI
Attentive Company Values
Default to Action - Move swiftly and with purpose
Be One Unstoppable Team - Rally as each other’s champions
Champion the Customer - Our success is defined by our customers' success
Act Like an Owner - Take responsibility for Attentive’s success
Learn more about AWAKE, Attentive’s collective of employee resource groups.
If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.
At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation. Attentive is also committed to providing reasonable accommodations for candidates with disabilities. If you need any assistance or reasonable accommodations, please let your recruiter know.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
