Operate directly with the CEO and CTO to scale Swiftly’s sales and business infrastructure. Own CRM hygiene, pipeline management, follow-up cadence, deal-stage definitions, dashboards, forecasting, and repeatable sales processes. Bridge customer needs with product and engineering, prepare executives for calls, track commitments, and drive execution. Support competitive research, pricing analysis, presentations, and other strategic priorities in an evolving, high-growth environment.
Swiftly is the AI platform purpose-built for retail, serving retailers, wholesalers, and brands. Swiftly's AI agents unify data, automate workflows, and power the marketing that drives measurable business growth. Swiftly AI is built on the industry's largest proprietary retail dataset: live transactions, 9 million products, and the closed-loop campaign outcomes of 33,000 stores.
Trusted by leading retailers, wholesalers, and hundreds of iconic brands, Swiftly unifies data across the retail ecosystem to accelerate growth and power the connected, personalized experiences that drive lasting shopper loyalty.
Position Summary:
Swiftly is searching for a highly ambitious, hands-on operator to join the company as our Founders Staff, working directly alongside our CEO and CTO, two of Swiftly’s founders, as we scale the company into its next stage of growth. This is not a traditional Chief of Staff role, this role will have a front-row seat to how the business is built and scaled, with meaningful ownership over the systems, processes, and strategic initiatives that help us operate more effectively and accelerate growth. Early focus will be strengthening the operating infrastructure around our sales motion, building repeatable processes, creating greater visibility into the pipeline, driving disciplined follow-through, and helping turn opportunities into execution.The Founders Staff will operate at the intersection of customers, product, engineering, and commercial strategy, joining customer conversations, understanding both the business and technical context behind what customers need, and translate those insights into action across the organization. We’re looking for someone who is ambitious, intellectually curious, and energized by building. Someone who sees an opportunity to make something better and wants the ownership to go make it happen. The scope of this role will evolve as Swiftly grows, giving the right person an opportunity to put their stamp on how we scale while working closely with the founders who built the company.
For someone who wants to accelerate their career, operate close to consequential decisions, and play a meaningful role in taking a high-growth technology company to the next level, this is a unique opportunity to do exactly that.
Strong preference for candidates based in Pacific Time Zone to support real-time collaboration with our core team.
Responsibilities Include:
- Own the sales operating system: Design and run the follow-up cadence, deal-stage definitions, and CRM hygiene so nothing falls through the cracks
- Manage the pipeline: Keep deals moving, chase next steps, prep the CTO before calls, draft and send follow-ups, track commitments made to prospects and customers
- Build repeatable process: Turn ad hoc sales motions into documented, repeatable playbooks; from first outreach through close and handoff to onboarding
- Bridge sales and product: Sit in on customer and prospect calls, understand technical requirements and objections, and translate them into clear input for product and engineering
- Prep and follow through: Own pre-call research and briefs, post-call recaps and action items, and make sure commitments made in a meeting happen afterward
- Report on the business: Build and maintain simple dashboards/reporting on pipeline health, conversion, and forecast so the Senior Leadership Team has visibility without having to ask
- Be a general operator: Jump into whatever's needed; competitive research, pricing analysis, deck prep, as the highest-priority work shifts week to week
- Other related duties as assigned
Required Qualifications:
- Master of Business Administration or equivalent advanced degree
- 8+ years of experience in business management, operations, strategy, or management consulting
- A builder's mindset: Proven ability to drive operational improvements and deliver measurable results
- Extreme attention to detail: excellent communication and presentation skills, ability to translate technical information
- Comfortable with ambiguity: energized, not stressed, by a role whose scope will evolve, take ownership
- Technical and product fluency: understand how the product works, ask technical questions and know what the engineering trade-offs are and mean
- Sales instincts: understand what makes a deal move (or stall), what good pipeline hygiene looks like, and how to build a follow-up cadence that doesn't feel robotic
- This position is not eligible for visa sponsorship. Applicants must be authorized to work in the U.S. without the need for current or future sponsorship
Preferred Qualifications:
- 6+ years of experience at a top-tier consulting firm (e.g., BCG, McKinsey, Bain)
- Familiarity with CRM tools (e.g., HubSpot, Salesforce) and building process inside them
- A technical background (prior engineering/PM role, or equivalent hands-on experience)
#LI-Remote
Note: This position is not eligible for visa sponsorship. Applicants must be authorized to work in the U.S. without the need for current or future sponsorship.
Working For Swiftly
We are working on a set of problems that require the best in the industry to get right. Our employees are the pillars of the future of the company and they are treated and compensated as such. We're a growing team of experienced industry professionals building an organization that can solve tough problems and values a collaborative environment.
Every Swiftly employee:
-Has demonstrated the ability to work collaboratively in an ambiguous, fast-paced environment
-Takes ownership of their domain from the ground up, from inception through deployment to customers
-Leaves their ego at the door and ensures the best idea leaves the room
-Is always experimenting with new technologies and learning new skillsets
If you've ever wanted to work on a project that blends a gorgeous consumer experience, sophisticated logistics, and scale that rivals the largest technology players, Swiftly is the place for you.
Equal Opportunity Employer
Swiftly is an Equal Employment Opportunity and Affirmative Action Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.
Swiftly will make reasonable accommodations in compliance with the Americans with Disabilities Act of 1990. Reasonable accommodations are available for qualified individuals with disabilities throughout the subsequent application process.
Similar Jobs
Artificial Intelligence • Enterprise Web • Software • Design • Generative AI
Designs and owns Webflow’s foundational cloud and source-control infrastructure, including multi-account landing zones, networking, DNS, PKI, secrets, Infrastructure as Code, GitHub delivery pipelines, self-service hosting patterns, policy guardrails, observability, cost controls, and security baselines. Partners with SRE, security, and developer productivity teams to improve reliability, scalability, adoption, and performance while managing cloud vendors and tooling relationships.
Top Skills:
AnsibleAWSAzureDatadogDnsFinopsGCPGithub ActionsGrafanaPkiPrometheusPulumiTerraformVpc
Financial Services
Designs, develops, tests, and delivers secure reusable frameworks, SDKs, and developer tools for enterprise engineering teams. Builds AI-native components with agent interfaces, CLIs, and documentation; implements security, resiliency, and observability by default. Analyzes adoption and health data to improve components, contributes to engineering communities, and supports team onboarding. Requires advanced Java, JavaScript, or Python skills, enterprise software development experience, SDLC and agile knowledge, and familiarity with cloud, AI, or machine learning.
Top Skills:
Artificial IntelligenceCi/CdClisCloud-NativeInfrastructure As CodeJavaJavaScriptLogsMachine LearningMetricsObservabilityPythonSdksTraces
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handles inbound calls and warm leads, consults customers on insurance needs, recommends appropriate coverages, and converts prospects into policyholders. The role includes paid Property and Casualty licensing and sales training, customer communication, brand representation, and working a schedule of four weekdays plus one weekend day. Employees work remotely using company-provided equipment and must maintain a dedicated workspace with wired high-speed internet.
Top Skills:
Cable/Fiber/Dsl High-Speed InternetPc
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
