Woolworths chief information officer Clive Whincup will leave the retailer on June 30 after more than two years in the top IT job.
His next moves are currently unclear.
Whincup's departure follows the appointment of new Woolworths CEO Brad Banducci in February.
Chief technology officer Ryan Fahy is acting in the CIO role while the retailer looks for a replacement.
Whincup has spent the past two years completing and realising the benefits of an organisation-wide Google technologies rollout, implementing a customer-centred design framework, improving underlying critical IT, and exploring the potential for newer technologies like 3D printing and the internet of things.
More recently his team has been looking at using digital and analytics technologies to bring real-time, online offerings to customers within physical stores.
"I think that's a whole new opportunity space that we've only just started to explore," Whincup told a Chair in Digital Economy event last year.
"One of the challenges we have to overcome is ... we don't know customers are in the store until they're leaving. And there is a real opportunity to turn that around, to know when they are in the store and what we can do with them while they're in the store."