At Upland Capital Group, we take pride in the work atmosphere we cultivate. We believe that building a strong team of "we entrepreneurs" and letting them work their magic sets us up as a company, and as individuals, for long-term success. We combine the people-focused values of traditional companies with the innovative problem-solving of a start-up. Founded by industry veterans in 2021, we are currently a company of 80+ employees and are growing rapidly.

Are you a "we entrepreneur"? If so, you value the individual freedom to practice your craft, but you understand and enjoy the benefits of working as a team. Your style is your style, and we aren't here to cramp it. We have a company culture and structure that gives you the freedom to do what you do best: your job. We think work should be fun, and we do our best to remove any obstacles that might get in the way of that for our team members.

The Chief Talent Officer (CTO) is a new role for a strategic leader to create mission-critical People Operations across the employee life cycle – recruiting, renewing, retaining, rewarding, & releasing. Reporting to the CEO, this person will deliver transparent and people-first programs to support the company’s growth and make Upland the best place for specialty underwriters to practice their craft.

Responsibilities: Support the CEO to advance and evolve Upland’s values-driven cultural in a rapidly growing, remote-first organization that prioritizes talent.

• Engage as a thought partner for company’s executives and leadership teams on organizational development and behavior topics
• Support business in addressing challenges and opportunities which come with a rapid growth:
  • Increase communication effectiveness & engagement in a remote-first environment of “we entrepreneurs”
  • Speed, quality, and diversity of talent acquisition
  • Effective and timely onboarding new team members
  • Developing leadership and coaching ability of managers
  • Performance management that contributes to performance improvement
• Build modern HR systems and processes to support Upland’s “we entrepreneur” strategy:
  • Scalable and flexible with minimum bureaucracy
  • Treat Upland’s employees as “fully-formed adults”
  • Attract the talent who fits company’s culture well
  • Combining “self-service” capabilities with “white glove” approach where it matters

Requirements: 10+ years of broad HR experience, including 5+ years of leading HR functions in the financial or professional services. Insurance experience a plus, but not required. Strong candidate will demonstrate experience in the following ways:

• Providing consultative and strategic approach to HR issues while having a direct connection and fingerprints on the work that needs to be completed
• Building HR function in a PE-backed, high-growth, remote-first, start-up with 100+ employees
• Delivering results in areas of responsibilities above that enabled company outperformance
• Providing insightful situation advice to managers
• Building data-driven action plans for talent assessment, performance management, total rewards, and engagement
• Ability to thrive in ambiguity and be a strong self-starter