Holly Bossert. (she, her)

Director of Sales at HR Acuity
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(386) 825-5501

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Matt Orozco

Being a good sales leader is hard, being a great one is even harder. From my experience, what makes a great sales leader is their ability to understand the individual needs of each team member while balancing the needs of the team to drive the greatest probability for everyone to succeed. From that description, it's easy to understand why it is so hard to find great sales leaders. Holly is that sales leader. She is someone who I literally followed from one great company to another great company, and who embodies the traits described above to a tee. One of her greatest assets is being able to take on the role of player and coach. For me, the best sales leaders are the ones who don't want to sit on the sidelines. They don't force themselves into the game, but they are there when you need them and are keen enough to know when to offer their assistance. I believe Holly derives that intuition from her ability to roll her sleeves up (figuratively mostly, but also literally) and be willing to help with whatever is needed. It's really hard to be a great sales leader, but Holly demonstrates this ability through empathetic leadership, constructive coaching, and unwavering support to her team!

Melissa Mavlanova-August

Holly is a seasoned senior sales leader with an impressive ability to lead and scale successful commercial teams. Holly's team are always at the top of the sales leaderboard and receive consistent shout outs for success during our monthly company calls. Holly leads practically, with empathy and an innate ability to understand people. She has developed an impressive team of successful leaders who deliver with grace and a smile - you can always 'tell' who's on 'Holly's team'... Holly is also a seasoned DE&I leader. She was pivotal to the founding of DE&I at Peakon. During, and since, the founding phase, she has offered strategic counsel, guidance and advocacy across the business - including at Executive level. She also dedicated a significant amount of time outside of work to support the delivery key strategic deliverables such as our Council and wider team operating model. She leads on the wider business activity as she understands the impact it has on employee experience and bottom line. I have been fortunate enough to have the opportunity to learn a lot from her. Through working in close collaboration, over time we developed a reciprocal coaching relationship which developed my commercial and leadership capability. I highly recommend her as an esteemed colleague with integrity.

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Credentials

  • Mental Health First Aide
    Mental Health First Aid (MHFA) England
    Jul, 2022
    - Nov, 2024
  • Enterprise GTM School
    Pavilion
    Feb, 2022
    - Nov, 2024
  • CRO School
    Pavilion
    Jul, 2021
    - Nov, 2024
  • Safe Sport Trained
    US Centers for Safe Sport
    Sep, 2018
    - Nov, 2024

Experience

    • United States
    • Software Development
    • 1 - 100 Employee
    • Director of Sales
      • Sep 2022 - Present

      You can’t prevent every employee relations issue. But you can control how your organization responds. Achieve consistency in the way you track, investigate, and analyze with HR Acuity — the employee relations case management solution. We empower you with structure, content, and tools around documentation, investigations, and data analytics. Our software equips you with built-in expertise to make best practice your process. HR Acuity. Because in today’s world, doing things the right way… Show more You can’t prevent every employee relations issue. But you can control how your organization responds. Achieve consistency in the way you track, investigate, and analyze with HR Acuity — the employee relations case management solution. We empower you with structure, content, and tools around documentation, investigations, and data analytics. Our software equips you with built-in expertise to make best practice your process. HR Acuity. Because in today’s world, doing things the right way is your only option. Show less You can’t prevent every employee relations issue. But you can control how your organization responds. Achieve consistency in the way you track, investigate, and analyze with HR Acuity — the employee relations case management solution. We empower you with structure, content, and tools around documentation, investigations, and data analytics. Our software equips you with built-in expertise to make best practice your process. HR Acuity. Because in today’s world, doing things the right way… Show more You can’t prevent every employee relations issue. But you can control how your organization responds. Achieve consistency in the way you track, investigate, and analyze with HR Acuity — the employee relations case management solution. We empower you with structure, content, and tools around documentation, investigations, and data analytics. Our software equips you with built-in expertise to make best practice your process. HR Acuity. Because in today’s world, doing things the right way is your only option. Show less

  • Your Sales Prophet
    • United States
    • Founder
      • Jan 2022 - Present

      At Your Sales Prophet we step in to help coach SMB and Mid-sized sales orgs effectively taking that lift off the Founder or VP. This allows those leaders to focus on strategic planning to grow the business while we focus on the day to day process. At Your Sales Prophet we step in to help coach SMB and Mid-sized sales orgs effectively taking that lift off the Founder or VP. This allows those leaders to focus on strategic planning to grow the business while we focus on the day to day process.

    • United States
    • Think Tanks
    • 700 & Above Employee
    • Chief Member
      • Sep 2021 - Present

      Chief is a private network built to drive more women into positions of power and keep them there. Chief is the only organization specifically designed for senior women leaders to strengthen their leadership journey, cross-pollinate ideas across industries, and affect change from the top-down. Chief is a private network built to drive more women into positions of power and keep them there. Chief is the only organization specifically designed for senior women leaders to strengthen their leadership journey, cross-pollinate ideas across industries, and affect change from the top-down.

    • United States
    • Think Tanks
    • 400 - 500 Employee
    • Executive Member
      • Feb 2021 - Present

      The Revenue Collective is building the largest community of sales and marketing executives at growth-focused companies in the world. The Revenue Collective is building the largest community of sales and marketing executives at growth-focused companies in the world.

    • United Kingdom
    • Technology, Information and Internet
    • 1 - 100 Employee
    • Vice President of Sales
      • Aug 2021 - Sep 2022

      As the pioneer in "TrustTech", Vault Platform's mission is to protect businesses and their people from risk with a better way of revealing and resolving workplace misconduct. You can't build an amazing workplace culture without trust and accountability. Vault provides a safe space for employees to report workplace misconduct as well as the ability for resolution tracking. As the pioneer in "TrustTech", Vault Platform's mission is to protect businesses and their people from risk with a better way of revealing and resolving workplace misconduct. You can't build an amazing workplace culture without trust and accountability. Vault provides a safe space for employees to report workplace misconduct as well as the ability for resolution tracking.

    • United States
    • Software Development
    • 1 - 100 Employee
    • Vice President of Global Sales- interim
      • Aug 2020 - Aug 2021

      By combining the power of employee surveys, customer feedback and unlimited 360 feedback, Macorva can identify standout employees who impact employee and customer engagement at all levels across the organization. Flagging your standout employees allows leaders to develop a plan to address problem areas, recognize contributions and ensure each team has capable and effective leaders. By combining the power of employee surveys, customer feedback and unlimited 360 feedback, Macorva can identify standout employees who impact employee and customer engagement at all levels across the organization. Flagging your standout employees allows leaders to develop a plan to address problem areas, recognize contributions and ensure each team has capable and effective leaders.

    • United States
    • Human Resources Services
    • 100 - 200 Employee
    • Director of Sales USA
      • 2018 - Aug 2020

      We are a data company - not a survey company - and this allows us to provide insights that will transform your business. Some of our customers have reduced their churn by 50%, others have completely restructured their organizations. We don't just measure engagement, we drive real change. We believe every employee’s opinion is valuable. That’s why we built the most inclusive and accessible solution in the industry. At the end of the day we help your company make better people… Show more We are a data company - not a survey company - and this allows us to provide insights that will transform your business. Some of our customers have reduced their churn by 50%, others have completely restructured their organizations. We don't just measure engagement, we drive real change. We believe every employee’s opinion is valuable. That’s why we built the most inclusive and accessible solution in the industry. At the end of the day we help your company make better people decisions. Show less We are a data company - not a survey company - and this allows us to provide insights that will transform your business. Some of our customers have reduced their churn by 50%, others have completely restructured their organizations. We don't just measure engagement, we drive real change. We believe every employee’s opinion is valuable. That’s why we built the most inclusive and accessible solution in the industry. At the end of the day we help your company make better people… Show more We are a data company - not a survey company - and this allows us to provide insights that will transform your business. Some of our customers have reduced their churn by 50%, others have completely restructured their organizations. We don't just measure engagement, we drive real change. We believe every employee’s opinion is valuable. That’s why we built the most inclusive and accessible solution in the industry. At the end of the day we help your company make better people decisions. Show less

    • Australia
    • Software Development
    • 700 & Above Employee
    • Global Director Enterprise Sales
      • May 2017 - Jun 2018

      In this role I built and lead a team of high performing enterprise sales executives across three of our four global offices. We focused on the largest and most complex organizations to help guide them in finding an employee engagement solution to drive culture and change within their organizations. Our Saas platform focused on engagement, moments that matter in an employees life cycle as well as DE&I.

    • Enterprise Sales Lead
      • Aug 2016 - May 2017

      Lead all b2b sales of employee engagement Saas platform for large and complex organizations across the US. Pioneered the enterprise business to determine market demand prior to a full enterprise team launch and development.

    • Vice President
      • Jun 2015 - Jul 2016

      At SMD I oversaw and drove all new sales in HR analytics to include employee surveys (internal customer voice), 360 assessments, hiring analysis, and turnover analytics through targeted marketing campaigns, online and virtual presentations to C-suite leaders, conferences, and roundtables. I managed the sales process from initial client contact to signature on the contract creating a lasting, positive first impression of SMD. At SMD I oversaw and drove all new sales in HR analytics to include employee surveys (internal customer voice), 360 assessments, hiring analysis, and turnover analytics through targeted marketing campaigns, online and virtual presentations to C-suite leaders, conferences, and roundtables. I managed the sales process from initial client contact to signature on the contract creating a lasting, positive first impression of SMD.

    • United States
    • Hospitals and Health Care
    • 700 & Above Employee
    • Nat Dir of Sales Employee and Physician Engagement and Education
      • Dec 2012 - Jun 2015

      (Press Ganey purchased Morehead Associates) In my role at Press Ganey I oversaw the new business sales for employee, physician, and volunteer engagement products. In this position I was responsible for bottom of the funnel sale as well as serving as the product matter expert via onsite and virtual presentations to the C-suite along side the assigned territory sales lead. I also assisted the sales team in developing sale strategies for complicated or larger clients, scoping projects… Show more (Press Ganey purchased Morehead Associates) In my role at Press Ganey I oversaw the new business sales for employee, physician, and volunteer engagement products. In this position I was responsible for bottom of the funnel sale as well as serving as the product matter expert via onsite and virtual presentations to the C-suite along side the assigned territory sales lead. I also assisted the sales team in developing sale strategies for complicated or larger clients, scoping projects, and negotiating contracts. Show less (Press Ganey purchased Morehead Associates) In my role at Press Ganey I oversaw the new business sales for employee, physician, and volunteer engagement products. In this position I was responsible for bottom of the funnel sale as well as serving as the product matter expert via onsite and virtual presentations to the C-suite along side the assigned territory sales lead. I also assisted the sales team in developing sale strategies for complicated or larger clients, scoping projects… Show more (Press Ganey purchased Morehead Associates) In my role at Press Ganey I oversaw the new business sales for employee, physician, and volunteer engagement products. In this position I was responsible for bottom of the funnel sale as well as serving as the product matter expert via onsite and virtual presentations to the C-suite along side the assigned territory sales lead. I also assisted the sales team in developing sale strategies for complicated or larger clients, scoping projects, and negotiating contracts. Show less

    • Director of Business Development
      • Oct 2009 - Dec 2012

      Morehead Associates was purchased by Press Ganey At Morehead Associates I was responsible for bringing in all new business and forming the foundation for a lasting relationship between clients and the Morehead team. My experience in both the clinical and nonclinical setting allowed me to fairly assess an organization's needs and guide them in the right direction. Morehead Associates was purchased by Press Ganey At Morehead Associates I was responsible for bringing in all new business and forming the foundation for a lasting relationship between clients and the Morehead team. My experience in both the clinical and nonclinical setting allowed me to fairly assess an organization's needs and guide them in the right direction.

    • United States
    • Hospitals and Health Care
    • 700 & Above Employee
    • Account Executive
      • Jul 2007 - Oct 2009

    • English Teacher
      • 1997 - 2004

Education

  • Lycoming College
    BA, English

Community

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