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Founding Customer Success Lead - Dealops

Why Dealops?

AI is transforming how companies price, sell, and scale. The rise of usage-based and hybrid pricing has unveiled a $25B+ market opportunity, demanding intelligent solutions that redefine every element of the go-to-market engine - from pricing strategy and deal execution to forecasting and sales compensation.

Founded by former Stripe leaders with deep expertise in pricing and GTM strategy, and backed by top investors including Pear VC, General Catalyst, and industry leaders from OpenAI, Stripe, and Slack, Dealops is pioneering this shift with AI-driven tools that empower businesses to adopt flexible pricing, streamline workflows, and maximize sales performance.

Join us and help build the future of pricing and selling in an AI-powered world!

Role overview:

We’re looking to hire our Founding Customer Success Lead to join the founding team at Dealops.

This is a strategic, high-impact role for someone who wants to be hands-on with customers and help build the function from the ground up. You’ll work directly with Sales, RevOps, and Finance leaders at some of the most exciting tech companies - understanding their goals, shaping their workflows, and helping them adopt and scale with Dealops.

You’ll partner closely with the CEO and wear multiple hats across Customer Success, Support, Product and Solutions Engineering to play a key role in unlocking expansions and driving retention.

If you love solving real problems with real customers, thrive in fast-paced environments, and want to help define how GTM teams operate in the AI era - we’d love to meet you.

What you’ll do:

  • Own the pre- and post-sale experience for customers end to end - from POCs through onboarding, implementation, and ongoing success.

  • Provide exceptional support via multiple channels, addressing inquiries and resolving issues with speed and care

  • Partner with Sales and Product to design and implement customer-specific workflows and configurations

  • Run A/B tests, analyze pricing performance, usage data, etc. to present enablement and expansion opportunities to customers

  • Build a scalable Customer Success motion - develop training, documentation, and tooling that help customers go from zero to one confidently

  • Act as the voice of the customer -  surface feedback, share insights, and help shape the product roadmap

  • Collaborate with Engineering to troubleshoot issues and roll out features that drive adoption and expansions

  • Take a “whatever it takes” mindset to unblock customers and deliver value quickly

What you have:

  • Experience: 3+ in a Customer Success / Solutions Engineering / Sales or BizOps role, ideally at an early-stage startup

  • Analytical skills combined with story telling: You thrive in spreadsheets but are also comfortable presenting to a room of 100s of sales reps, running QBRs with buyers, etc.

  • Customer management: Proven ability to work directly with enterprise and mid-market customers - you can lead calls, drive projects forward, and align stakeholders

  • Domain knowledge: Experience working in B2B Sales Tech or GTM tooling is a strong plus

  • High standards: You care deeply about doing great work and helping others do the same

  • Ownership mindset: You take full responsibility for outcomes and thrive when given autonomy

  • Location: Excited to work in-person out of our office in San Francisco

Average salary estimate

$100000 / YEARLY (est.)
min
max
$80000K
$120000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Founding Customer Success Lead - Dealops, Pear VC

At Dealops, we’re on a mission to revolutionize how businesses approach pricing and sales through cutting-edge AI technology, and we're thrilled to announce that we're hiring a Founding Customer Success Lead in Austin, TX! This role is perfect for someone passionate about empowering customers and looking to create lasting relationships in the tech space. As our Founding Customer Success Lead, you’ll partner with high-level leaders across Sales, RevOps, and Finance to understand their unique goals and design workflows that enhance their experience. You’ll oversee the entire customer journey, from pre-sale to post-sale, ensuring a seamless onboarding experience and incredible ongoing support. If you're eager to step into a pivotal role where your insights and efforts can significantly impact our customers’ successes, this is for you! You'll also play a crucial role in building our Customer Success function from scratch. Your analytical skills will shine as you run A/B tests and analyze performance data to identify and communicate expansion opportunities. Plus, you'll act as the voice of the customer, providing essential feedback that helps shape our product roadmap. If you thrive in a fast-paced environment and have a proactive, solutions-oriented mindset, we can’t wait to meet you. Join us at Dealops and help lead the charge into an AI-powered future—where flexible pricing becomes the standard, and every customer interaction is a chance to create value!

Frequently Asked Questions (FAQs) for Founding Customer Success Lead - Dealops Role at Pear VC
What are the key responsibilities of the Founding Customer Success Lead at Dealops?

The Founding Customer Success Lead at Dealops will take on a variety of responsibilities that are crucial for creating exceptional customer experiences. This includes managing the entire customer journey—overseeing everything from Proof of Concepts (POCs) to onboarding and ongoing support. It's also about collaborating closely with Sales and Product teams to tailor workflows and configurations specific to each customer’s needs.

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What qualifications are needed to apply for the Founding Customer Success Lead position at Dealops?

To be successful in the Founding Customer Success Lead role at Dealops, candidates should have a minimum of three years of experience in Customer Success, Solutions Engineering, or similar roles. Moreover, having a strong analytical background and exceptional storytelling skills is essential, as is previous experience working directly with enterprise-level clients in a B2B Sales Tech or GTM context.

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What skills are essential for a Founding Customer Success Lead at Dealops?

Essential skills for the Founding Customer Success Lead at Dealops include exceptional customer management abilities, analytical capability combined with storytelling finesse, and a strong ownership mindset. The ideal candidate should be proficient at translating complex data into actionable insights while also demonstrating a willingness to take full responsibility for outcomes.

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How does the Founding Customer Success Lead contribute to the Customer Success function at Dealops?

The Contribution of the Founding Customer Success Lead is pivotal in establishing a scalable Customer Success function at Dealops. This includes developing training programs, crafting documentation, and creating tools that empower customers to transition from zero to one confidently. Furthermore, their feedback will shape the product roadmap by acting as the voice of the customer.

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What type of work environment can a Founding Customer Success Lead at Dealops expect?

At Dealops, the work environment is fast-paced and collaborative. As a Founding Customer Success Lead, you will work directly with cross-functional teams and be empowered to take initiative and ownership of your work. This role is ideal for someone who thrives in a dynamic setting, where innovation and customer-centric solutions are front and center.

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Common Interview Questions for Founding Customer Success Lead - Dealops
Can you explain your experience in managing customer relationships as a Founding Customer Success Lead?

When answering this question, focus on specific examples where you've successfully managed enterprise or mid-market customer relationships. Discuss how you addressed their needs, resolved issues, and contributed to their overall satisfaction. Highlight your approach to communication and how you maintained strong relationships through regular check-ins.

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How would you approach developing a Customer Success strategy from the ground up?

In your response, outline your strategy by emphasizing the importance of understanding customer needs and mapping out their journey. Discuss how you'll leverage analytics to inform decision-making and the steps you'll take to create training and support materials that resonate with different customer segments.

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What methods do you use to analyze customer data to identify expansion opportunities?

Provide an overview of the analytical tools and methods you utilize to interpret customer data. Discuss your experience with A/B testing and how those insights inform customer engagement strategies. It’s beneficial to cite specific metrics you've analyzed in the past and how they led to successful outcomes.

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Describe a challenging customer situation you’ve faced and how you resolved it.

Here, you can share a specific incident that highlights your problem-solving abilities. Discuss how you calmed the situation, the steps you took, and the ultimate resolution. Emphasize your commitment to customer satisfaction and the lessons learned from that experience.

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How do you prioritize your workload when managing multiple customer accounts?

Discuss your strategies for workload management, particularly how you prioritize based on urgency and importance. Provide examples of tools or processes you’ve implemented in the past to ensure timely responses to customer needs, such as CRM software or project management platforms.

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What role do you believe a Founding Customer Success Lead plays in shaping the product roadmap?

Explain that the Founding Customer Success Lead acts as a critical liaison between customers and the product team. Emphasize how customer feedback gathered during interactions can provide invaluable insights that inform product enhancements and future development.

Join Rise to see the full answer
How would you design and implement customer-specific workflows?

Detail your approach to understanding a customer's specific needs and collaborating with cross-functional teams to create tailored workflows. Discuss the importance of documentation and training to ensure a smooth implementation and ongoing success.

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What do you think are the most important skills for a Founding Customer Success Lead?

Highlight essential skills such as strong communication, analytical thinking, customer empathy, and ownership. Discuss how being adaptable and proactive can help in anticipating customer needs and resolving issues before they escalate.

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How would you measure the success of the Customer Success function?

Explain that success metrics may include customer satisfaction scores, renewal rates, and expansion revenue. Talk about how you plan to set up feedback loops with customers to gather data for continuous improvement.

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What attracts you to the Founding Customer Success Lead position at Dealops?

Focus on what excites you about Dealops—a pioneer in AI-driven pricing solutions. Share your enthusiasm for joining a founding team and your vision of contributing to a dynamic environment that prioritizes innovation and customer-centricity.

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