Apply

Description

Parcel shipping is a massive, complex cost center — and most companies are still managing it manually, reactively, and inefficiently. That's the problem we exist to solve.

Sifted is a parcel spend management platform trusted by 3,500+ companies. We connect to a company's carriers once and take over the work their team doesn't have time for: analyzing every invoice, monitoring every carrier change, and automating the processes that used to live in spreadsheets.

What you'll be part of

We're at an inflection point. The product is leading the market, the customer results are real, and we're building the engine — to reach more of the right buyers at scale. You won't be walking into a finished machine. You'll be helping build it.

That means the work is meaningful, the pace is fast, and what you do here shows up in the numbers.

AI isn't a talking point here — it's how we work

SiftedAI Copilot is our flagship product and the core of everything we do. It's an always-on logistics analyst built across the entire SiftedAI platform, continuously monitoring our clients' parcel operations in the background and surfacing what actually needs attention.

That same standard applies internally. Every Sifted employee is expected to use AI to work faster, think sharper, and deliver more. Mastering AI tools isn't a nice-to-have. It's core to how we operate and how we stay ahead.

If this sounds like your kind of place

You're motivated by real problems, measurable outcomes, and being part of a team that's moving from good to great. If you want to do the best work of your career at a company where your contribution is visible and your growth is real, we'd love to talk.

About the role

As VP of Talent & People, you will serve as a strategic partner to the CEO and leadership team, owning the full people agenda during one of the most consequential chapters in Sifted’s history.

Your predecessor built a strong foundation — AI governance in policy, AI fluency in job descriptions and performance reviews, an adoption dashboard, and a culture of learning. Your charge is to evolve that foundation into a fully realized people strategy for an AI-native company.

This role carries three primary mandates: deepen and accelerate talent development as the nature of work evolves with AI, lead the organizational change management required as we move from AI-augmented to AI-operated, and sustain and scale the culture that makes Sifted a place where exceptional people do the best work of their careers.

RESPONSIBILITIES

Talent Development & AI-Era Workforce Strategy

Sifted’s AI adoption is real and measurable — 89% utilization company-wide, 100% in Engineering, 100% completion rate on AI tool training. The next chapter is about depth, not activation. You will:

• Evolve our AI fluency program from tool adoption to capability mastery — building a workforce that doesn’t just use AI, but thinks, designs, and operates with it at the center of their workflows.*
• Develop career pathing and role evolution frameworks that reflect the structural shifts underway, including Sifted’s migration toward Product Engineer roles and the AI-first reorganization of engineering.*
• Build a forward-looking talent development architecture — structured learning, mentorship, stretch assignments, and leadership development — tuned to the pace and demands of an AI-native company.
• Partner with functional leaders to anticipate and address capability gaps created by the next generation of AI automation, and translate those gaps into hiring, reskilling, and succession strategies.*
• Own talent acquisition strategy, ensuring Sifted can attract mission-driven, AI-curious professionals across all functions in a competitive market for top AI-era talent.*

Organizational Change Management

Sifted’s evolution from traditional SaaS to AI-operated logistics platform is a fundamental transformation — in roles, workflows, decision-making authority, and what it means to “do your job” well. The company is already moving. Your role is to lead the human architecture of that change. You will:

• Develop and execute a comprehensive change management strategy aligned to Sifted’s AI roadmap — from our current AI Automation phase through our AI-Operated future.*
• Create frameworks that prepare teams for evolving responsibilities as AI agents increasingly take over routine work, and help employees reimagine their roles as higher-order judgment, creativity, and relationship work come to the foreground.
• Lead internal communications strategy around transformation initiatives — ensuring clarity, consistency, and trust at every stage.*
• Partner with the CEO and executive team to assess organizational design needs that emerge from the AI roadmap, and implement structural changes with care, transparency, and a clear rationale.*
• Maintain and deepen the adoption feedback infrastructure already in place — our adoption dashboard, collaboration sessions, and monthly active user tracking — adding sentiment, change readiness, and employee experience dimensions.
• Build and maintain psychological safety for a team navigating real uncertainty about the future of work, making it possible for people to embrace change rather than resist it.

Culture & Employee Experience

AI adoption at Sifted is already deep and widespread — this role will build on that energy and shape a culture that is as distinctive and intentional as our product. You will:

• Define and steward Sifted’s cultural identity through the AI transformation — ensuring our values remain lived, visible, and meaningful as our team, tools, and business model evolve.
• Build employee experience programs that create belonging, recognition, and connection in a remote-first, AI-augmented work environment.
• Own the employee lifecycle — from onboarding (where AI governance and fluency are already integrated) through performance management, development, and offboarding — with programs that reflect Sifted’s progressive, people-first philosophy.*
• Act as a visible and trusted advocate for employees at the leadership table, collaborating closely with heads of Engineering, Product, Sales, Marketing, Client Success, and Operations to embed people strategy across the business.

People Operations & Compliance Infrastructure

You will build on and optimize the foundational systems already in place, and create the infrastructure for the next phase of Sifted’s growth demands.

• Own total rewards strategy — compensation, benefits, and equity — ensuring Sifted remains competitive in attracting and retaining AI-era talent. Partner with the CEO and CFO on headcount planning, salary structures, commission plans, and incentive program design.
• Manage enterprise Claude account operations: seat provisioning, permissions management, vendor relationship with Anthropic, and usage optimization — ensuring Sifted maximizes its investment in its primary AI platform.*
• Own payroll operations, HRIS administration (Paylocity), and partner with Finance on headcount reporting and compensation data integrity.*
• Administer employee benefits, 401(k), insurance renewals, and broker/vendor relationships.*
• Execute the annual performance management cycle end-to-end: 9-Box calibration, review design, manager coaching, SLT presentations, and delivery coordination.*
• Develop and enforce HR policies, employment agreements, contractor paperwork, and MNDA execution — ensuring all documentation is enforceable and precedent-aware.
• Assess and mitigate organizational risk across legal, compliance, employee relations, and cultural dimensions. Serve as the compliance owner for employment law and privacy regulations.
• Leverage the people analytics and adoption dashboard infrastructure already in place to drive evidence-based decisions across talent, retention, and organizational health.

Requirements

• 8+ years of progressive HR leadership experience, with demonstrated success in talent development and organizational change management.
• Proven track record leading people through significant organizational transformation — ideally including a technology pivot, rapid growth, or product category shift.
• Experience in a SaaS, technology, or data-driven environment, with genuine curiosity about AI and its implications for the workforce.
• Experience operating at the VP or Director level in a company of 50–150 employees, ideally during a scale or transformation phase.
• Strategic thinker and executional doer — equally comfortable designing a talent roadmap and rolling up your sleeves to build what comes next.
• Hands-on experience with Claude; familiarity with prompt engineering, AI-assisted workflows, and enterprise AI administration is a strong plus.
• Deep expertise in compensation design, including base, variable, and equity structures across roles and levels.
• Strong command of employment law, HR compliance, and privacy regulations; comfortable serving as the compliance owner.
• Exceptional communicator with the ability to lead difficult conversations, inspire confidence during uncertainty, and influence without authority.
• Deep empathy for the human experience of change, paired with the courage to drive it forward on an accelerated timeline.
• Data-literate and outcomes-oriented, with the ability to measure, communicate, and continuously improve the impact of people programs.
• Comfortable with ambiguity and energized by the challenge of building systems and culture in real time. Urgency and decisiveness in a fast-paced organization.
• You view culture not as a set of perks, but as an operating system — the way decisions get made, the way people treat each other, and the way the company shows up for its mission.
• Experience with Paylocity or a comparable HRIS platform highly preferred.

WHAT WE PROVIDE

• Well capitalized Private Equity investor focused on Growth
• Best-in-class compensation package and an unmatched comprehensive benefit program
• Flexibility to achieve and accomplish results
• Extremely collaborative work environment across teams to drive results
• Culture is built on how we improve people’s lives

*Denotes an essential function of the role. (Role to be based out of Overland Park, KS.)