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Title

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Senior Troublemaker

Description

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We are looking for a Senior Troublemaker to join our dynamic and forward-thinking team. This role is not for the faint of heart — it’s for the bold, the curious, and the relentless innovators who are not afraid to challenge the status quo. As a Senior Troublemaker, you will be responsible for identifying outdated processes, questioning conventional wisdom, and proposing bold, unconventional solutions that drive meaningful change across the organization. You will work closely with cross-functional teams to uncover inefficiencies, spark creative thinking, and champion a culture of experimentation and continuous improvement. Your role will involve pushing boundaries, asking the hard questions, and inspiring others to think differently. You’ll need to be comfortable navigating ambiguity, managing resistance, and turning chaos into opportunity. The ideal candidate is a strategic thinker with a rebellious spirit, excellent communication skills, and a proven track record of driving innovation in complex environments. You should be passionate about making things better — not just for the sake of change, but for real, measurable impact. You’ll need to be persuasive, resilient, and able to build trust with stakeholders at all levels. This is a unique opportunity to make a significant impact in an organization that values courage, creativity, and transformation. If you thrive in environments where rules are meant to be questioned and limits are meant to be pushed, we want to hear from you.

Responsibilities

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  • Challenge existing processes and propose innovative alternatives
  • Collaborate with teams to identify inefficiencies and areas for improvement
  • Lead brainstorming sessions and innovation workshops
  • Promote a culture of experimentation and calculated risk-taking
  • Communicate disruptive ideas effectively to stakeholders
  • Monitor industry trends and emerging technologies
  • Develop and pitch bold initiatives to leadership
  • Mentor teams on creative problem-solving techniques
  • Act as a catalyst for organizational change
  • Measure and report on the impact of implemented innovations

Requirements

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  • Proven experience in innovation, strategy, or change management roles
  • Strong critical thinking and problem-solving skills
  • Excellent communication and persuasion abilities
  • Comfortable with ambiguity and rapid change
  • Track record of challenging norms and driving results
  • Ability to influence and inspire across all levels of an organization
  • Creative mindset with a passion for experimentation
  • Bachelor’s degree in business, design, or related field (Master’s preferred)
  • Experience leading cross-functional initiatives
  • High emotional intelligence and resilience

Potential interview questions

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  • Can you describe a time you challenged the status quo successfully?
  • How do you handle resistance to change?
  • What’s the boldest idea you’ve ever implemented?
  • How do you foster creativity in a team?
  • What industries or trends are currently inspiring you?
  • How do you measure the impact of innovation?
  • Describe your approach to managing ambiguity.
  • What motivates you to disrupt traditional thinking?
  • How do you balance risk and reward in innovation?
  • What’s your process for identifying inefficiencies?