Strategic Sales Development Representative

Summary

Join Chili Piper as a Strategic SDR and bridge the gap between high-value prospecting and strategic business growth. Collaborate with the Strategic AE and Marketing to identify and engage key prospects within target accounts. You will build pipeline, create and refine processes, and shape the future of strategic sales. Responsibilities include identifying high-value prospects, crafting outreach strategies, collaborating on marketing campaigns, partnering with Strategic AEs, designing outbound campaigns, understanding prospect pain points, owning early-stage pipeline activities, shadowing the Strategic AE on demos, and collaborating cross-functionally. The role requires proven success booking meetings, engaging with multiple stakeholders, creative account-based targeting, strong research and analytical skills, exceptional communication skills, critical thinking, and the ability to work independently. Chili Piper offers competitive pay, unlimited vacation, generous health insurance, equipment/software, a professional development stipend, equity, and an annual company retreat.

Requirements

• Proven success booking meetings within this segment in the past
• Success engaging with multiple stakeholders within the 1 account and can speak to this strategy
• Evidence of creative account based targeting / approaches
• As the role may require you to attend in person meetings or conferences, access to major tech cities will be an advantage
• Strong ability to research, analyze, and synthesize data into actionable insights for strategic outreach
• Exceptional verbal and written communication skills, with the ability to craft messaging that resonates with senior-level audiences
• Demonstrated ability to think critically and strategically, especially in navigating complex sales processes and high-value opportunities
• Comfortable operating in a highly dynamic and fast-paced environment, with the ability to pivot quickly when needed
• Proven ability to work independently, take ownership of initiatives, and execute with minimal supervision
• Strong passion for understanding and articulating the value of Chili Piper
• Growth mindset and passion for professional development

Responsibilities

• Identify and research high-value prospects within target accounts, crafting tailored outreach strategies that resonate with senior decision-makers
• Ideate and execute on creative ways to crack into accounts and garner useful information to aid the sales cycle
• Collaborate with Marketing on out of the box campaigns, specifically focusing on target accounts
• Partner closely with Strategic AEs to refine and execute personalized engagement plans for top-tier accounts
• Design and execute outbound campaigns with a focus on high-impact strategies, leveraging insights to iterate and optimize efforts
• Develop a deep understanding of prospect pain points, industry trends, and competitive landscapes to deliver compelling value propositions
• Own early-stage pipeline activities, including initiating conversations, qualifying leads and ability to answer product related questions. It is worth noting here that all messaging, calls and meetings will be worked on collaboratively between the Strategic SDR and the Strategic AE
• Shadow the Strategic AE on demos
• Collaborate cross-functionally to contribute to the development of the sales process, tools, and strategies, ensuring alignment with Chili Piper’s broader business goals
• Represent Chili Piper at industry events, webinars, and discussions, building credibility and awareness within target markets

Preferred Qualifications

• Knowledge of Chili Piper’s platform and value proposition across our top accounts
• Passion for Chili Piper’s values: Help & Compassion, Innovate, Take Ownership, Growth Mindset, and Have Fun
• High emotional intelligence and interpersonal skills
• Resourcefulness and creativity in solving challenges
• Strong attention to detail, documentation, and follow-through
• Ability to thrive in a dynamic, global team environment

Benefits

• Unlimited vacation (and we do mean it, and we do take it!)
• Generous health, dental, and vision insurance
• Any equipment/software/tech that you need to do your job
• Annual professional development stipend of $2,000 USD
• Equity - all Pipers receive stock options
• Annual company retreat for a week of bonding and adventure (previous retreat locations include Paris, Morocco, Tulum, Iceland, Ibiza, and India!)