Sales Director – Managed Services

livingHR • Tampa, FL

1d • Remote

About The Position

Sales Director – Managed Services
Growth – Director
Location: Remote (see list of approved locations)
Type: Full-Time
The Position can be in any of our office markets/states (FL, CO, IL, MA, NH, RI, ME, CT, GA, SC, NC, TX)
Who We Are...
Let us introduce ourselves.
livingHR is the remote-first, professional services “work agency” created to make work better. We have served over 400+ organizations to provide human-centric, future-of-work ready, HR-managed services, professional services, and products to augment HR and People functions around the world.
livingHR believes in taking exceptional care of our team so they can take exceptional care of our clients, partners, and communities. We are adaptable, entrepreneurial, and always looking to iterate and make improvements, which can come with a lot of change (for the better). If you are looking for a role where no day is ever the same, and you prescribe to the idea that variety is the spice of life, then you will likely enjoy our way of working. The people who find the most success here are those who are willing to be a part of a team, where no task is too big or too small, and feedback is welcomed.
To learn more about our Culture Code, Cares Campaign, and our WeBelong work in Diversity, Equity, and Inclusion visit our website: https://livinghr.com/.

Requirements

• Bachelor’s degree (business, marketing, communications)
• 8-10 years of direct sales experience in HR consulting, managed services, HR outsourcing, People Ops, or similar solution-based environments.
• Strong understanding of the HR lifecycle and People Operations functions for companies under 500 employees.
• Experience selling strategic, retainer-based services (preferred).
• Excellent communication, discovery, and storytelling skills.
• Ability to build trust with executive buyers and HR leaders by understanding real HR challenges and presenting practical, scalable solutions.
• Experience collaborating with industry partners in a co-selling or referral capacity.
• Strong consultative selling skills with a proven record of meeting/exceeding quota.
• Proficiency in CRM tools (HubSpot preferred), reporting dashboards, and pipeline management.
• A self-starter able to own and grow a market from the ground up.
• Resilience, persistence, and strong time management.
• Communication Skills: Ability to clearly present ideas, influence stakeholders, and build relationships.
• Active Listening: Understanding client pain points and tailoring solutions accordingly.
• Negotiation & Persuasion: Balancing client needs with company goals, closing deals effectively.
• Customer Service Orientation: Building long-term trust and maintaining satisfaction post-sale.
• HR industry experience required, SaaS experience a plus
• Self-starter, entrepreneurial mindset, can own and build out a market strategically
• Product/Service Knowledge: Deep understanding of offerings and how they solve customer problems.
• Market Awareness: Understanding industry trends, competitors, and client business challenges.
• Consultative Selling: Ability to position solutions as strategic investments, not just transactions.
• Data Literacy: Comfort with CRM systems, sales dashboards, and pipeline/forecast tracking.
• Goal Orientation: Demonstrated history of meeting/exceeding quotas or KPIs.
• Resilience & Persistence: Ability to handle rejection and maintain motivation.
• Time Management: Prioritizing leads, managing accounts, and balancing prospecting with closing.
• Problem-Solving: Creative thinking to overcome client objections and internal challenges.
• Networking Skills: Building connections with clients, partners, and industry professionals.
• Collaboration: Working across marketing, product, and customer success teams.
• Account Growth: Ability to expand existing relationships, upsell, and cross-sell effectively.
• CRM Proficiency: HubSpot, , or industry-specific systems.
• Sales Enablement Tools: LinkedIn Sales Navigator and/or industry specific systems
• Digital Communication: Strong virtual selling skills (Zoom, Teams, email, social).
• Analytics & Reporting: Comfortable generating reports and making data-driven decisions.

Responsibilities

• Own the full sales cycle for HR Managed Services: prospecting, discovery, scoping, proposal development, and closing retainer-based engagements.
• Build and manage a strong pipeline of companies under 500 employees seeking ongoing HR support.
• Prospect into new accounts to develop relationships with founders, CEOs, CFOs, COOs, and HR leaders.
• Host and attend prospect/industry events to elevate awareness of livingHR’s Managed Services model.
• Build strategic partnerships with HR tech vendors, benefits brokers, and fractional CFO/COO networks to generate warm referrals.
• Collaborate with Marketing to co-create campaigns that generate inbound and outbound leads.
• Work closely with Delivery Leaders to structure thoughtful, strategic service packages and scopes of work.
• Represent livingHR professionally and act as a thought leader in HR operations, compliance, culture, and People strategy.
• Manage high-value client accounts post-sale, ensuring satisfaction and identifying opportunities for growth (e.g., special projects, assessments, talent solutions).
• Educate prospects on how our fractional and managed HR services work: onboarding, employee relations, compliance, compensation, payroll support, HRIS implementation, workflows, and culture programs.
• Lead consultative discovery calls to diagnose HR gaps, pain points, and operational inefficiencies.
• Partner with Delivery to shape service models that match client maturity, budget, and growth stage.
• Translate client needs into structured retainers—typically 20–160 hours/month depending on size and complexity.
• Collaborate with Delivery team to ensure scope alignment and client success after handoff.
• Identify opportunities to cross-sell additional support such as projects, DEIB work, change management, and talent acquisition support.
• Provide market insights on the evolving needs of small to mid-sized organizations and the challenges they face in HR.
• Work with finance and operations to develop accurate pricing models for retainer-based engagements.
• Partner with Marketing to shape messaging around People Ops, HR compliance, and fractional HR support.
• Maintain strong ethical standards, professionalism, and confidentiality in all interactions.

Benefits

• Autonomy & Flexibility: We call it, WfWiMS “Work from Where it Makes Sense,” a philosophy we have had in play since our inception in 2009, and we have no plans to change. This flexibility comes with a responsibility to self-manage and be an exceptional performer. We work remotely and have offices in our hub markets if you want to come in or go onsite with a client and from time to time, we do that too.
• Compensation: Competitive, fair, and transparent base salary plus incentives for account growth, retention, and client referrals.
• Comprehensive Benefits: We provide a wide range of benefits, including medical, dental, 401k, STD/LTD, life, and telehealth mental health counseling.
• Flexible PTO/Paid Holidays: We encourage you to use your time, with a minimum requirement, and provide 23 paid holidays.
• A Culture of Impact and Humanity: We care about the impact we make and the humanity we extend to each other, our clients, and our broader community.

What This Job Offers

• Job Type: Full-time
• Career Level: Director