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executive assistant and office manager Jobs in Chicago

executive assistant and office manager

executive assistant ceo

DRW Trading Group

<div>DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk.

Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets.

We operate with respect, curiosity and open minds. The people who thrive here share our belief that it's not just what we do that matters&ndash;it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus.

The Executive Assistant (EA) to the CEO provides strategic, high-touch support in a fast-paced, market-driven environment. This role serves as an extension of the CEO&mdash;owning complex scheduling and prioritization, managing sensitive communications, driving follow-through on critical initiatives, and coordinating across senior stakeholders internally and externally. The ideal candidate is highly proactive, exceptionally organized, discreet, and comfortable operating with autonomy amid rapidly changing priorities and time-sensitive matters.

What you will be working on:

Strategic Executive Support &amp; Time Optimization
<ul>
<li>Act as a trusted partner to the CEO, anticipating needs and proactively removing friction from day-to-day operations.</li>
<li>Anticipate issues and initiate appropriate action to ensure the most effective use of the CEO's time, including creating structure, prioritization frameworks, and clear daily/weekly rhythms.</li>
<li>Prepare the CEO for meetings by ensuring materials are complete, accurate, and delivered in advance; highlight key decisions, deadlines, and risks.</li>
</ul>
Complex Calendar, Travel &amp; Meeting Management
<ul>
<li>Coordinate internal and external meetings across multiple time zones; prepare and circulate agendas and materials; ensure timely follow-ups.</li>
<li>Coordinate logistics as needed (e.g., travel, virtual meeting setup, onsite arrangements), ensuring smooth execution.</li>
<li>Maintain personal and professional calendar and communicate adjustments/changes on a regular basis.</li>
</ul>
Cross-Functional Leadership &amp; External Partner Coordination
<ul>
<li>Coordinate with senior leaders and key teams (executives, trading, risk, compliance, legal, HR) to align schedules, track deliverables, and support business-critical workflows.</li>
<li>Maintain strong working relationships with internal stakeholders and external partners; represent the CEO's office with credibility and tact.</li>
</ul>
Executive Materials &amp; Operational Administration
<ul>
<li>Review incoming email and use judgement to assess urgency, remove irrelevant messages, provide standard reply, and escalate as required.</li>
<li>Draft partner communications and assist in preparing presentations.</li>
<li>Address other day-to-day administrative needs: filing, invoices, expense preparation, bills, tax documents, etc.</li>
<li>Provide personal support as needed while maintaining professionalism, discretion, and appropriate boundaries.</li>
</ul>
Skills and Competencies
<ul>
<li>Education: Bachelor's degree in Business Administration, Finance, Economics, or a related field; or equivalent professional experience.</li>
<li>7+ years of progressive experience supporting C-suite executives, including significant experience supporting a CEO or equivalent senior leader.</li>
<li>Industry Knowledge: Familiarity with financial markets, trading workflows, risk/compliance concepts, and market hours.</li>
<li>Executive-level communication skills (written and verbal) with strong judgment, polish, and the ability to interface credibly with senior leadership and external partners.</li>
<li>Exceptional organizational and time-management capabilities; proven ability to handle high volume, competing priorities, and last-minute changes.</li>
<li>Highly proactive and autonomous&mdash;able to identify needs, propose solutions, and drive outcomes without extensive direction.</li>
<li>Demonstrated discretion and integrity; trusted with confidential information and sensitive relationships.</li>
<li>Problem-solving mindset, proactive approach, and the ability to anticipate needs before they arise.</li>
<li>Adaptable and resilient; able to support extended hours during market events, urgent matters, or key deadlines.</li>
</ul>
Work Environment
<ul>
<li>Fast-paced, high-intensity trading environment; high standards for accuracy and speed.</li>
<li>On-site presence preferred/required at the office; sensitive to market hours and international time zones.</li>
<li>May involve evening or weekend work around major market events or key deadlines.</li>
</ul>
The annual base salary range for this position is $100,000 to $200,000 depending on the candidate's experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long-term disability, life and AD&amp;D insurance, health savings accounts, and flexible spending accounts.

For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at https://drw.com/privacy-notice.

California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice.

#LI-DW1</div>

Executive Assistant, CEO

House Buyers of America

<div>House Buyers of America is looking for an Executive Assistant. The Executive Assistant will be responsible for supporting our fast paced, growth-oriented CEO. This position requires a minimum of 3 years of experience supporting executives. This position requires a high level of accuracy, attention to detail, and the ability to work independently and solve problems. We are looking for someone who will be available after regular hours when needed and able to handle critical deadlines on a moment's notice. This position is FULLY REMOTE!

What you will do:
<ul>
<li>Manage and prioritize the CEO's calendar/schedule.</li>
<li>Manage CEO's inbox to include screening, managing, and responding to emails and incoming communications, ensuring timely responses and prioritizing urgent matters.</li>
<li>Provide executive administrative support for project(s) by performing analyses and preparing appropriate supporting documentation to support and assist the executive leadership team.</li>
<li>Coordinates adherence to deadlines and completion of special projects, correspondence, and reports. Provides executive administrative support by developing and refining presentations as required by members of the executive leadership team.</li>
<li>Plan and organize meetings.</li>
<li>Sit in on meetings and report back to CEO and communicate CEO priorities in meetings.</li>
<li>Bid out vendors and key resources needed by company. Negotiate the best pricing and terms.</li>
<li>Assists with development and preparation of various reports and schedules under the direction of the assigned Executive or department professionals.</li>
<li>Compose, edit, and proofread correspondence, contracts, reports and/or presentations.</li>
<li>Responsible for updating task management software for key action items.</li>
<li>Responsible for communication support across the practice area.</li>
<li>Compile meeting agendas and minutes as needed.</li>
<li>Perform routine administrative tasks such as filing and drafting correspondence.</li>
<li>Read and analyze incoming memos, submissions, and reports to determine their significance and plan their distribution.</li>
<li>Prepare responses to correspondence containing routine inquiries.</li>
<li>Maintain strict confidentiality of the company and executive information.</li>
<li>Occasionally interview candidates.</li>
<li>Performs various administrative functions as requested.</li>
</ul>
About You:
<ul>
<li>3+ years of related experience as an executive assistant</li>
<li>10+ years of administrative experience</li>
<li>Strong communication skills (both written and verbal)</li>
<li>Strong skills within MS Office Suite</li>
<li>Ability to develop presentations and materials that are client and/or executive management ready</li>
<li>Associate's degree from an accredited university required; Bachelor's degree from an accredited university preferred</li>
</ul>
Why we are a great place to work:
<ul>
<li>Our company is FULLY REMOTE</li>
<li>Our awesome company culture includes: competitive pay great benefits, great people, casual dress, team events, work hard/ play hard environment</li>
<li>2025 Revenue is up 60% year over year compared to 2024</li>
<li>2025 Ratified acquisitions are up 70% year over year compared to 2024</li>
<li>Q4 2025 sales are up 100% compared to Q3 2025</li>
<li>Q4 2025 revenue is up 152% compared to Q4 2025</li>
<li>Q4 Ratified acquisitions are up 64% compared to Q4 2025</li>
<li>We are continuing our nationwide expansion, now operating in 44 states plus Washington, DC.</li>
</ul>
House Buyers of America is a leading national home-buying company helping homeowners sell with confidence through a simple, transparent, and hassle-free process. Founded in 2001 and operating in 44 states, the company blends decades of real estate expertise with technology-driven operations to deliver speed, certainty, and consistent outcomes. House Buyers of America has been recognized for its industry impact, including Ernst &amp; Young Entrepreneur of the Year and inclusion on the Inc. 5000 list of America's fastest-growing companies.

House Buyers is an equal opportunity employer and does not discriminate by sex, creed, race, or by age. www.HouseBuyersOfAmerica.com

Total Compensation Range: $60,000- $100,000/ year</div>

Executive Assistant (Remote)

Claire's

<div>
 
 
 Role Summary
 
 
 
 
 
 
 Seeking a strategic, proactive Executive Assistant to partner with the CEO/President in managing
 
 
 complex operations across portfolio companies, ownership groups, and functional leadership. This role
 
 
 demands exceptional organizational capabilities, business experience and knowledge, and diplomatic
 
 
 relationship management.
 
 
 
 
 
 
 Key Responsibilities
 
 
 
 
 
 
 
 Operational Excellence
 
 
 
 &bull; Maintain sophisticated tracking systems for priorities, deliverables, and deadlines across multiple
 
 
 workstreams
 
 
 &bull; Manage complex calendar across time zones, stakeholder priorities, and strategic initiatives
 
 
 &bull; Synthesize information from diverse sources into actionable briefings and decision-ready materials
 
 
 &bull; Prepare concise 1-pagers distilling key issues, recommendations, and context
 
 
 
 
 
 
 Strategic Support
 
 
 
 &bull; Anticipate needs and proactively address priorities before being asked
 
 
 &bull; Contextualize meetings, materials, and correspondence within broader business strategy
 
 
 &bull; Connect dots across functional areas (retail ops, merchandising, finance, HR) and identify
 
 
 dependencies
 
 
 &bull; Translate between technical/operational details and executive-level insights
 
 
 
 
 
 
 Stakeholder Management
 
 
 
 &bull; Navigate complex reporting relationships with portfolio company leadership and private equity
 
 
 ownership
 
 
 &bull; Exercise CEO proxy authority while respecting organizational boundaries and leader autonomy
 
 
 &bull; Build credibility to drive follow-through across functions without direct authority
 
 
 &bull; Balance assertiveness in execution with diplomatic relationship stewardship
 
 
 
 
 
 
 Required Qualifications
 
 
 
 &bull; 5+ years supporting C-suite executives in complex, multi-stakeholder environments
 
 
 &bull; Demonstrated business judgment and ability to operate independently
 
 
 &bull; Track record of managing competing priorities in fast-paced settings
 
 
 &bull; Exceptional written/verbal communication and synthesis skills
 
 
 &bull; Experience in retail, private equity, or operational environments preferred
 
 
 
 
 
 
 Success Profile
 
 
 
 You're two steps ahead, not waiting for direction. You convert chaos into clarity. You understand when
 
 
 to push, when to defer, and how to get things done through influence rather than authority.
 
</div>

Executive Administrative Assistant

Chicago Family Health Center

<div>Description:

About Chicago Family Health Center (CFHC)
Chicago Family Health Center (CFHC) is dedicated to providing accessible, high-quality, and compassionate healthcare to individuals and families across Chicago&rsquo;s diverse communities. We promote wellness and health equity through comprehensive care and community partnerships.
We are seeking a strategic and detail-oriented Executive Office Manager to support our Chief Executive Officer (CEO) and C-Suite leadership team. This pivotal role ensures smooth day-to-day operations of the executive office and drives organizational excellence through proactive administrative leadership and operational coordination.
Position Summary
Reporting directly to the CEO, the Executive Office Manager serves as a key liaison between executive leadership, the Board of Directors, and internal/external stakeholders. The position requires exceptional organizational, communication, and problem-solving skills to anticipate the needs of the CEO and executive team. The ideal candidate demonstrates initiative, confidentiality, and a strong sense of professionalism in managing multiple priorities and complex projects.
Key Responsibilities:
Executive Support<ul><li>
Serve as the primary liaison between the CEO, C-Suite executives, Board of Directors, and external partners.</li><li>
Manage executive calendars, coordinate meetings, and organize recurring leadership and management events.</li><li>
Prepare agendas, materials, and presentations; document and track follow-up items from meetings.</li><li>
Draft, proofread, and distribute high-level correspondence, reports, and communications.</li><li>
Coordinate travel and logistics for executive team members and major organizational events.</li><li>
Oversee executive-level projects, reports, and cross-departmental initiatives.</li><li>
Ensure confidentiality, accuracy, and professionalism in all communications and documentation.</li></ul>
Board of Directors Liaison<ul><li>
Plan and coordinate logistics for Board and committee meetings, including scheduling, communications, and materials.</li><li>
Record and maintain official Board documents, including minutes, bylaws, and rosters.</li><li>
Manage communication and event coordination for Board-related activities.</li><li>
Track and follow up on Board action items in partnership with leadership.</li></ul>
Office Management &amp; Operations<ul><li>
Oversee day-to-day operations of the executive suite, including supplies, facilities, and vendor relationships.</li><li>
Maintain organized records, filing systems, and office equipment.</li><li>
Coordinate office and technology needs for the C-Suite team.</li><li>
Manage office cleanliness and organization, working with building facilities as necessary.</li><li>
Support logistics for staff meetings, retreats, and organization-wide events.</li></ul>
Work Environment &amp; Schedule<ul><li>
Hybrid work arrangement: Three days on-site / Two days remote (subject to operational needs).</li><li>
Occasional evening or weekend work required.</li><li>
Travel between CFHC locations as needed.</li><li>
Typical office environment with moderate noise level.</li></ul>
Chicago Family Health Centers offers benefits to all its full-time employees:
BCBS Medical PPO Plans| BCBS Dental |VSP Vision| Tuition Reimbursement up to $1,500 per year|8 Paid Holidays plus 4 floating holidays |10 Days of vacation |2 personal days | 10 sick days |
Requirements:

Education and Experience<ul><li>
Bachelor&rsquo;s degree in Business Administration, Communications, or a related field required.</li><li>
Minimum of five (5) years supporting senior executives (CEO, COO, CFO, or equivalent) in a fast-paced environment.</li><li>
At least three (3) years of project management experience.</li><li>
Experience in healthcare, nonprofit, or mission-driven organizations preferred.</li><li>
Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint).</li><li>
Familiarity with collaboration tools such as Microsoft Teams, Zoom, and/or RingCentral.</li><li>
Experience with project management platforms (Asana, Trello, or similar).</li></ul></div>

Executive Office Manager

American Lung Association

<div>The American Lung Association has an excellent opportunity for a Director, Executive &amp; Governance Operations. Working as a member of the Executive Office department, you will join an outstanding group of professionals dedicated to our mission: to save lives by improving lung health and preventing lung disease through research, education, and advocacy.
The Director of Executive &amp; Governance Operations is a senior operational role responsible for managing operational and governance support functions of the President &amp; CEO, National Board of Directors and Executive Leadership Team. Reporting to the Chief Inclusion, Engagement &amp; Governance Officer, this role ensures disciplined execution, continuity and accuracy across Board processes and enterprise operations. This role also serves as project manager for the annual work plan and key strategic initiatives, ensuring coordinated execution, progress tracking, and alignment with organizational priorities, while overseeing all associated financial, contractual, and logistical responsibilities.
Location: The position is located at the American Lung Association&rsquo;s Chicago, Illinois office and will be a hybrid of in-person and virtual work.
Responsibilities:
Board &amp; Governance Operations<div><ul><li>
Partner with Chief Inclusion, Engagement &amp; Governance Officer (CIEGO) to finalize board meeting agendas, annotated agendas, materials and minutes. Manage the Board portal and ensure timely posting of materials in accordance with Board donation guidelines and the organizational Bylaws.</li><li>
Manage, monitor, track and report individual contributions in accordance with board donation guidelines; accounting for any related discrepancies and reconciliations.</li><li>
Manage, monitor and track annual conflict of interest forms ensuring 100% compliance.</li><li>
Partner with board committee leads to oversee the annual processes to update committee charges, goals and membership, ensuring compliance with committee composition requirements as outlined within the Bylaws.</li><li>
Manage corporate governance records, including resolutions, annual conflict of interest forms, the corporate seal, and signature tracking.</li><li>
Track governance calendars, compliance items, and annual documentation requirements.</li><li>
Orient board members to the travel program and process board reimbursements and travel donations.</li></ul></div>
 CEO &amp; Executive Office Operations<div><ul><li>
Manage the administrative operations of the CEO, including the CEO&rsquo;s calendar, travel, AMEX expenses and executive correspondence to ensure the CEO&rsquo;s priorities and schedule are well coordinated.</li><li>
Provide input to the budgets for the Executive Office and the National Board of Directors, supporting planning, financial oversight and accountability.</li><li>
Oversee the organization&rsquo;s corporate credit card program, including coordination with American Express to resolve issues, managing cards for new and departing staff, and monitoring adherence to organizational policies.</li></ul></div>
 Meeting and Event Management<div><ul><li>
Direct all national meeting operations on behalf of executive leadership and in partnership with senior leadership, creating and maintaining an annual meeting calendar.</li><li>
Assess meeting needs and budgetary considerations to efficiently and effectively plan, project manage and implement all meeting logistics for regional and national meetings, conferences and workshops.</li><li>
Oversee hotel and restaurant procurement and accounts payable processes to include cultivating relationships with hospitality managers, soliciting bids, and negotiating and executing contracts pursuing rates and terms that protect the financial health of the organization and minimizes risk; and processing related invoices.</li><li>
Direct all meeting registration operations for regional and national meetings and events to include creating, launching and monitoring registration processes and collecting related fees.</li><li>
Partner with hospitality managers to ensure high quality execution of the terms of the contract and specifications for hotel and meeting rooms, onsite events and meals.</li><li>
Maintain current knowledge of event planning standards and trends by participating in on-line seminars, consulting with other professionals and reading trade publications.</li></ul></div>
Travel Program<div><ul><li>
Develop and socialize official staff and non-staff travel policy and procedures, implementing mechanisms for compliance to include tracking, securing and storing signed acknowledgements; and monitoring monthly travel reports and resolving issues related to non-compliance.</li><li>
Manage daily operation of travel program, providing authorized lists, obtaining budget codes and handling problems as necessary, and reviewing, coding and processing monthly credit card bill for airline travel.</li></ul></div>
Strategic Initiatives Project Management<div><ul><li>
Partner with the CIEGO to develop status updates, summaries, dashboards, and progress reports for the CEO, ELT, and governance leaders.</li><li>
Ensure alignment across planning calendars, governance timelines, and executive reporting cycles.</li><li>
Collaborate with the CIEGO to support timely updates and provide assistance with revisions and refinements as needed.</li></ul></div>
Volunteer and Staff Recognition Program<div><ul><li>
Direct all annual volunteer and staff recognition program operations in partnership with the Executive Leadership Team to include overseeing nomination solicitation and review processes, confirming and onboarding reviewers, directing the scoring and selection processes, and supporting all related communications.</li><li>
Create and implement annual awards ceremony in partnership with board and staff leaders to include the event program and run of show, awardee preparations, event materials and logistics, awards and certificates, and travel.</li></ul></div>
Qualifications:<div><ul><li>
Bachelor&rsquo;s degree in business administration, Nonprofit Management, Communications, or a related field, or an equivalent combination of education and experience. Relevant professional certification (e.g., PMP, CMP, CAE) a plus.</li><li>
Minimum 8-10 years of progressive experience in executive operations, board governance, project management, or enterprise administrative leadership.</li><li>
Demonstrated experience supporting C‑suite executives, Boards of Directors, and senior leadership teams, preferably within a national nonprofit or complex, matrixed organization.</li><li>
Proven experience managing Board governance processes, including meeting planning, agendas, minutes, portals, compliance tracking, and bylaw‑driven requirements.</li><li>
Experience organizing large‑scale meetings, conferences, and events, including vendor procurement, contract negotiation, budget management, and on‑site execution.</li><li>
Experience producing executive updates: status reports, progress summaries, decision logs, and briefing memos for executive audiences.</li><li>
Experience managing operational budgets and expenses, with accountability for financial stewardship, compliance, and internal controls.</li><li>
Ability to travel 4-5 times per year as needed.</li><li>
Ability to lift approximately 25 lbs. (supplies).</li><li>
Consistent with its mission, the American Lung Association maintains a smoke-free workplace; all employees must abstain from tobacco use in any form, including vaping.</li></ul></div>
Compensation: Exact compensation may vary based on skills, experience, and location. The target hiring range for this position is between $85,000 and $95,000 per annum.
Benefits: The Lung Association offers a comprehensive benefits package including:<div><ul><li>
Paid Leave - 10 vacation days in the first year (15 days thereafter), 2 personal days and 15 sick days per year, as well as 12 company-paid holidays per year. We also offer Paid Parental Leave for eligible employees.</li><li>
Insurance - Employees (and their eligible dependents) can enroll in our medical, dental, and vision plans, as well as voluntary plans for critical illness, accident, hospital indemnity, short-term disability and supplemental life/AD&amp;D insurance. Employees will be enrolled in company-paid life/AD&amp;D and long-term disability Insurance coverage.</li><li>
Retirement Plan - Eligible employees can participate in our 401(k) Defined Contribution Retirement Plan, which offers matching employer contributions (up to 4%) and year-end discretionary non-elective contributions.</li></ul></div>
Equal Employment Opportunity
The American Lung Association is an equal opportunity employer. It is the policy of the American Lung Association to prohibit discrimination and harassment of any type and to provide equal employment opportunities to employees and applicants, without regard to their race, color, sex, sexual orientation, age, marital status, religion, national origin, alienage or citizenship status, genetic predisposition or carrier status, or physical and/or mental disabilities, veteran status, or any other status protected by law.
Policy Statement
It is the policy of the American Lung Association to prohibit discrimination and harassment of any type and to provide equal employment opportunities to employees and applicants, without regard to their race, color, sex, sexual orientation, age, marital status, religion, national origin, alienage or citizenship status, genetic predisposition or carrier status, or physical and/or mental disabilities, veteran status, or any other status protected by law. This policy applies in all employment actions including recruitment, hiring, promotions, transfers, corrective actions, terminations, compensation, benefits and training.</div>

Director, Executive & Governance Operations

Occulytics Inc.

Head of SalesThe Opportunity The senior living industry struggles to understand why 92% of its leads don't convert. Occulytics provides the data and tools to materially improve that conversion rate, helping operators understand their market, pinpoint wasted spend, and drive occupancy.We are seeking a foundational Head of Sales to build and lead our commercial engine. This is more than a sales role; it's a career-defining opportunity to establish our platform as the new industry standard, building the entire revenue function from the ground up.You will be the architect of our sales function, operating as a high-impact individual contributor to hunt and close our most important deals. You will simultaneously build the playbook, processes, and GTM strategy that will serve as the foundation for our future sales organization.Key ResponsibilitiesSales Strategy &amp; Execution (Player)<ul><li>Spearhead the complete, full-cycle sales process from lead generation and prospecting to complex contract negotiation and close.</li><li>Design and execute creative outreach strategies targeting senior living operators and investors.</li><li>Architect and deliver compelling proposals, presentations, and ROI analyses demonstrating how Occulytics solves the &quot;92% problem.&quot;</li><li>Structure and negotiate complex, multi-year subscription agreements, ensuring a smooth handoff to the client success team.</li></ul>Go-to-Market Development (Builder)<ul><li>Partner directly with the CEO to refine market segmentation, ideal customer profiles, pricing, and competitive positioning.</li><li>Create the foundational sales infrastructure: build the playbook, define sales stages, and implement rigorous pipeline management and forecasting in our CRM.</li><li>Act as the &quot;voice of the market,&quot; providing structured prospect feedback to the product and leadership teams to guide the roadmap.</li><li>Identify and cultivate high-leverage channel and referral partnerships to accelerate lead generation.</li></ul>Relationship &amp; Thought Leadership (Evangelist)<ul><li>Represent Occulytics at key industry conferences, roundtables, and webinars, establishing our credibility and brand.</li><li>Become a trusted advisor to prospects and clients, maintaining deep knowledge of senior living sales, marketing, and operations trends.</li></ul>What You Bring (Qualifications)Required Experience<ul><li>5+ years of experience in B2B sales, business development, or a senior sales/marketing leadership role.</li><li>Proven track record of exceeding quotas and closing new-logo deals in a &quot;hunter&quot; capacity.</li><li>A &quot;builder&quot; mentality: You thrive in ambiguity, love creating structure from scratch, and are eager to build and scale repeatable systems.</li><li>Executive presence: You communicate with a high degree of confidence and credibility, capable of engaging C-suite leaders.</li><li>Data-Driven: You manage your pipeline and forecast with rigor and accuracy (experience with HubSpot, Salesforce, or similar CRM is essential).</li></ul>Preferred Experience<ul><li>Experience within the senior living industry, either in a sales/marketing leadership role at an operator or in a sales role at a technology vendor serving the market.</li><li>A strong, active network of relationships with C-suite and regional leaders in the senior living industry.</li></ul>Skills &amp; Attributes<ul><li>Strategic &amp; Tactical: You can design a 12-month GTM strategy in the morning and cold-call a key prospect list in the afternoon.</li><li>Self-Motivated: You are an entrepreneur at heart, comfortable owning ambitious revenue targets and operating with a high degree of autonomy.</li><li>Curious &amp; Passionate: You have a genuine passion for innovation in senior living and a deep curiosity about data-driven decision-making.</li></ul>Why You'll Love It Here<ul><li>Build from the Ground Up: You won't just run a playbook; you'll write it. This is your chance to build a high-performance sales organization from first principles.</li><li>Direct CEO Partnership: You will report directly to the CEO, serving as a key strategic partner in shaping the company's GTM strategy and future.</li><li>Direct Impact: Your work will be pivotal to Occulytics' success and will visibly shape the future of the senior living industry.</li><li>Define the Category: Join a fast-growing company poised to redefine how senior living communities use data to solve their most expensive problems and drive growth.</li></ul>Occulytics Inc. is an equal opporunity employer.Pay: $140,000.00 - $160,000.00 per yearBenefits:<ul><li>401(k)</li><li>401(k) matching</li><li>Dental insurance</li><li>Flexible spending account</li><li>Health insurance</li><li>Health savings account</li><li>Paid time off</li><li>Relocation assistance</li><li>Vision insurance</li></ul>Application Question(s):<ul><li>Walk us through a pipeline you built from scratch &mdash; what channels did you own, what worked, and what did you learn?</li><li>How have you approached selling into a niche or relationship-driven industry where trust matters more than volume?</li><li>What does your ideal sales process look like from first touch to close, and how have you built or refined that process at a previous company?</li><li>We're an early-stage SaaS company in senior living. How would you think about the first 90 days in this role?</li><li>Tell us about a deal you lost. What happened and what would you do differently?</li><li>WIll you require visa sponsorship to work in the United States now or in the future?</li></ul>Work Location: Hybrid remote in Chicago, IL 60611

Head of Sales

Ventas, Inc.

<div><h1 class="jobSectionHeader">Job Description:
</h1>Ventas is a leading S&amp;P 500 company enabling exceptional environments that benefit a large and growing aging population. With an enterprise value exceeding $50 billion and a portfolio of more than 1,400 properties across North America and the United Kingdom, Ventas is a preeminent participant in the longevity economy. Its largest business is private-pay senior housing, which includes over 850 communities providing valuable care and services to more than 90,000 residents. The Ventas portfolio also includes outpatient medical buildings, research centers and healthcare facilities that attract strong institutional demand from the largest health systems, biomedical companies and universities and other research institutions in the world. Backed by strong financial performance and a collaborative culture, Ventas has the capital, capabilities and relationships to deliver superior value. The experienced Ventas team shares a commitment to each other and to the Company&rsquo;s mission of helping people live longer, healthier, happier lives.
About the Role
The Financial Analyst, Financial Planning &amp; Analysis (FP&amp;A) supports core forecasting, financial modeling, and analytical processes that drive portfolio and enterprise performance. This role works closely with a team of analysts and cross-functional partners to enhance forecasting models, develop presentation materials, analyze business trends, and support strategic decision-making. The Analyst will also prepare materials for senior and executive leadership, including monthly business reviews, quarterly earnings, board presentations, investor materials, and other ad hoc analysis.
Key Responsibilities
<ul><li>Compare forecast against results and create detailed variance analyses.
</li><li>Analyze financial performance and communicate trends, insights, and findings to management.
</li><li>Support the continued development and enhancement of forecasting models and analytical tools.
</li><li>Gather and consolidate data from multiple sources to inform forecasting, planning, and strategy.
</li><li>Monitor KPIs and leading indicators to improve forecast accuracy and business insights.
</li><li>Create high-quality presentations for internal and external audiences, including monthly business reviews, earnings calls, board meetings, and investor presentations.
</li><li>Identify opportunities for new reporting, tools, or models to support company initiatives and growth.
</li><li>Engage frequently with senior and executive leadership (SVPs, CEO, CFO) to support data-driven decision-making.
</li><li>Conduct ad hoc reporting and analysis as needed.
</li><li>Collaborate with and periodically travel to operators and assets to deepen portfolio knowledge and relationships.
</li></ul>Qualifications
<ul><li>Bachelor&rsquo;s degree in business, accounting, finance, real estate, or a related field.
</li><li>1+ years of experience in budgeting, forecasting, financial modeling, analytics, reporting, planning, or similar fields.
</li><li>Must be located in the Chicago, IL surrounding area or willing to relocate for the duration of employment.
</li><li>Willingness to adapt and thrive in a blended work environment with 3-days in office, seamlessly transitioning between remote work and in-office operations.
</li><li>Understanding of financial statements (income statement, balance sheet, cash flow).
</li><li>Strong financial modeling skills in Microsoft Excel; experience with Cube functions is a plus.
</li><li>Experience with visualization or presentation tools (e.g., PowerPoint, Tableau).
</li><li>Must be legally authorized to work in the United States without need for employer sponsorship now or in the future
</li></ul>The estimated base salary range for this position is $70,000 &ndash; $95,000 per year. This range reflects a good‑faith estimate of the base salary Ventas reasonably expects to pay at the time of posting. Actual base pay will be determined based on work location, skills, qualifications, relevant experience, and business needs.
In addition to base salary, this role is eligible for discretionary incentive compensation and a comprehensive benefits package, which includes medical, dental, vision, retirement savings, paid time off, and other wellness benefits under applicable plan terms.
Ventas, Inc. offers a competitive compensation and benefits package to the successful candidate.
Ventas, Inc. is an Equal Opportunity Employer.
Ventas, Inc. does not accept unsolicited resumes from staffing agencies, search firms or any third parties.</div>

Financial Analyst, FP&A

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