with Jessica Gilmartin, Chief Marketing Officer of Calendly Jessica’s pivotal career moment  When Jessica turned 20, she fulfilled her dream of living in Paris. Although this was initially a frightening step, Jessica has always drawn on this experience as a way to reinforce that she is capable of taking risks which were reinforced by her subsequent city relocations and starting her own business. Jessica’s Current Role as CMO at Calendly Despite having 10 million users and strong organic and viral growth, Calendly only introduced a sales and marketing team 8 years after it’s initial launch, and this team is expanding. The role of CMO at Calendly allows Jessica to leverage her strengths and experiences in creating a product-led growth business and integrating different types of sales and marketing motions.  Jessica feels a cultural alignment to Calendly and a genuine love for the product. Know the people, know the data, know the story Jessica introduces us to a great quote she learnt from a previous leader at Asana – “What makes a great CMO is someone that knows the people, knows the data and knows the story.” Jessica explains how she applied this mindset in her first 30 days of the CMO role at Calendly. Methods Jessica used to get to know the people at Calendly The Magic Wand conversations. Jessica would ask her team members in 1:1 discussions, “If I had a magic wand, what would you like me to fix”? This was a great question to dive deep into what the challenges are (as well as discover what is working well). Trust building was crucial for Jessica, especially given her arrival would initiate transformative change in the marketing team. Jessica built trust through practising psychological safety behaviours such as admitting to her mistakes, actively encouraging team members to vocalise disagreements, and showing her team that she is a real human being who genuinely cares for her team.  Having difficult yet productive and crucial conversations within the team is very important to Jessica; she sees trust as a key enabler of this.  Learning, building, iterating. Throughout her exploratory discussions (and note-taking) with the team, Jessica identified themes that she was continually iterating, validating and exploring/learning until she felt stable enough in her knowledge to move towards execution.  Transparency Following Jessica’s team exploration, she shared her (1) work plan (2) 30 day observation plan and (3) draft objectives (which was open to return feedback) to her team. The team appreciated that not only were these plans made transparent - they were also created based on team feedback. This created valuable team buy-in.  Values. Jessica sought input from the team on the culture and values they would like to commit to in order to perform their best work. This iterative process has now resulted in a finalised set of values for the Calendly marketing team.   Getting to know the customers was important to Jessica, and she would regularly get involved in customer engagement activities, such as participating in customer calls. The Outcomes. Jessica reports that she has a happy team that's motivated, energised and excited to work together, which she sees as crucial. Understanding the Story: Jessica emphasises the importance of identifying the story and brand perception of the organisation in the marketplace, although she admits that this objective has a reasonably long lead time. Jessica explains that it is also essential to identify and communicate the right story of the marketing team to internal audiences (such as the executive team) to ensure the marketing team receives strong support. Jessica achieves this by regularly meeting the executives, sharing visions, and owning mistakes and failures.  Understanding the Data - As a former investment Banker, Jessica knows how crucial data is. As part of her first 90 days, Jessica has been focused on what marketing data is currently available and what is needed going forward with th