Pillar was founded in 2025. Today, we are 90+ people, serve 1000+ customers, raised €15.2M (pre-seed and seed round) and are expanding internationally.

We are building the financial operating system for construction: bringing AI, automation and modern software to an enormous industry still full of slow, fragmented processes.

We are looking for a Head of Customer Success who loves people who build things, believes every customer should get real value from Pillar and wants to grow a team that customers trust.

Why join now

Over 1000 construction companies run their numbers, job sites and documents on Pillar. Our Customer Success team takes care of them from the day they sign: onboarding, adoption, renewals and upsell. Now the first big renewal waves are coming, new modules are launching and we are growing abroad. We need someone who turns a fast-growing team into a clear, measurable engine for retention and growth.

The mission

Make every customer successful with Pillar: lead and grow the Customer Success team, own retention and expansion, and make sure what customers live every day reaches the people who build the product.

What you will do

• Lead and grow the Customer Success team, who report directly to you.

• Own the customer journey after signature: onboarding, adoption, renewals and upsell.

• Own net revenue retention and churn, with clear targets and a plan to reach them.

• Build a health score that works, using product usage and sentiment, and act early on accounts at risk.

• Prepare the team for the renewal waves, with playbooks that start well before the renewal date.

• Bring the voice of the customer to Product and Engineering, and help prioritise what matters most.

• Work side by side with Sales, Support and Product, so every customer has one clear experience.
  

Who we are looking for

People leaders who care about customers and love a measurable result

• You have led a Customer Success team in B2B SaaS, ideally in a scaleup after product-market fit.

• You have managed CSMs directly: hiring, coaching, setting goals and helping them grow.

• You have owned retention numbers: NRR, GRR, churn and expansion, and you can show how they moved.

• You have built CS operations: segmentation, health scores, onboarding and renewal playbooks.

• You are commercially confident: you are comfortable with renewals, upsell and difficult conversations.

• You are data-driven: you work with tools like HubSpot and product analytics and act on what you see.

• You speak product: you turn customer feedback into clear, prioritised input for Product.

• You are AI-native: AI is already part of how you work and how your team takes care of customers.

• Native or fluent Italian and professional English, Spanish is a big plus. Based in Barcelona or happy to relocate.

• Nice to have: experience with customers in several countries, vertical SaaS, fintech or construction.

How we work

• Small squads, high autonomy, no unnecessary layers.

• AI-first, in the product and in the way we take care of customers.

• Close to customers: every conversation is a chance to learn something about the product.

• Pillar is not for you if you are looking for a mature Customer Success machine to run. We are building it, and you will lead it.
  

Hiring process

01 CV screening

02 30-min People call with Marta

03 1-hour conversation with Lorenzo, usually in person

04 Business case, prepared at home (3 to 4 hours)

05 Business case presentation with Lorenzo (1 hour, online)

06 Conversations with our co-founders Paolo and Gabriel

07 Optional: meet our Customer Success Team

What we offer

• Gross salary 70.000-90.000 €, based on experience

• A real leadership seat: you will shape how Pillar takes care of every customer after signature, not just run someone else’s playbook

• A team to grow: Customer Success Managers who report to you and want to learn from you

• Impact you can measure: retention and expansion are among the numbers that matter most for our next stage

• A direct line to the product: what you hear from customers turns into features and fixes

• Our Barcelona hub, with Italian roots and a team that works across Italy, Spain and beyond

• People who care: a team that celebrates wins together, gives honest feedback and has fun along the way.