Global Sales Training & Enablement at CreatorIQ
How do you define enablement?
Giving people what they need to crush it at their jobs and do their best work
Describe your current role.
I build airplanes midflight. I say that because sales never really stops. There are always moving pieces in my projects. I am a team of one at CreatorIQ and my scope of work is across the board. I'm responsible for the sales team communications, administering Lessonly, and managing internal content, I helped moderate some product webinars and most recently -- I'm hosting our company wide All Hands, which I love doing. However, most of my work is with our sales leadership team. It is impossible to scale a team without a game plan and the sales managers are influential key players so I stay close to make sure I'm in lock step with them.
Every day is different and more than half of my time, I am collaborating across departments. I build courses in Lessonly. I create learning landscapes for BDRs to grow into AEs. I onboard new sales reps. I get to do all of this because of all the other smart people in our business. I work to curate content and synthesize ideas for our customer-facing teams to leverage.
Nothing gets done without focus. I go all in on the biggest need of the revenue business and then I pick my head up and go in on the next one. When things get busy and we're going to market with a new product feature in our platform or something, my world becomes a gorgeous chaos. And that's a good thing because I get bored quickly.
At each company I've been with, I always enjoy spending time with customer-facing teams because they move fast. A factor of happiness at a job is liking your customer and in enablement, my "customers" are the front line reps and their managers. And yeah, I like them.
Briefly walk through your journey to get where you are today.
I started at Sprinklr in NYC after cold emailing the hiring manager. I researched her all over social media to find her contact. Following my passion for public speaking, I got hired to onboard all new employees during the company's hyper growth stages when they were hiring like crazy. I left the company to move to Houston with my then-boyfriend (stupid decision) but we broke up before it happened. I guess they got wind that I was still unemployed. After some months, they asked me to come back to join the Field Enablement team. I knew a lot about Sprinklr and not much about sales. I didn't even know what "Field Enablement' meant. I had to learn a lot of the sales skills and product knowledge on the fly and I gained an incredible understanding of it by pure osmosis. I was assisting in these week-long boot camps 1-2 times a month. My boss was Dick Dunkel and not only did I get a deep understanding of MEDDPICC but I learned so much about body language, tonality, and empathy by just watching how he held himself in all the sessions. At the time, Sprinklr was experiencing a lot of personnel changes at the top and the GTM content would have to align with our sales play. It was stressful but it forced me to be flexible and taught me how to over communicate.
Then I got recruited to work on the Sales Enablement team at Procore in California. There were like 9-10 people on the team which was crazy to me because at Sprinklr, we were a team of 3. I was responsible for getting all the important information in the business to the field, effectively. I doubled down on my writing skills, presentation skills, and cross-collaborative mindset. My first boss was Alex Jaffe and he changed my life. He taught me how to ask easy, clarifying questions and how to work with more senior-level executives. In effect, this increased my professional confidence. My second boss was Lia Cefalu and she showed me the importance of delivering excellent experiences - from training to celebrating wins to hyping people up. In Enablement, you are introducing new programs or new processes. Whatever new thing you are launching, it is important to stick it the first time because people will remember if it was great, if it was terrible, if it was a waste of time, if they want to do it again, etc. Later on, this forced me to ask the question "how do we want reps to feel after this?" every time I ran our Global Sales All Hands.
And now I'm at CreatorIQ, where I'm thankful to be on the team with Kojo Amako who I knew from our past Sprinklr days. :)
I specifically call out my managers because my journey would not be what is today if it wasn't for their investment in me.
What’s your proudest accomplishment?
The company was growing fast and we were changing our sales landscape. Big changes. I'm talking new comp plans, new quotas, new sales leaders, and we were introducing a brand new segment to the business. There was a lot happening and it was happening fast. Depending on your territory, things affected you differently. I remember hearing about this and assuming the company has evolved like this before. Rumors were starting in the field. There was confusion.
Then, my boss told me that everything before this was incremental. This would be the largest shift to the revenue organization at this size.
I was at the airport gate when I got a ping from my boss's boss to help write up a communication for the sales managers so they are a) educated b) aligned and c) empowered to share the news with their teams. I opened my computer on my lap and went to work straight away - laying out the facts, tying stakeholders to specific changes, writing copy, just brain dumping all of the information. And then I started to simplify and simplify and simplify. I enjoy getting into that flow state and working my magic on messaging because I have to put myself in the recipient's shoes.
It was EOQ and I knew that the teams needed to mainly have their general expectations set for now. The specific details could wait until the next quarter when my audience has more headspace. So I kept the language clear and simple. Lastly, I sent out these lightweight "communication packets" to every VP and figured they can massage the wording or delete some phrases, etc. Before I boarded the plane, I saw a handful of VPs forward a lot of the copy I wrote, just as is. Imagine that - you can air out the confusion and uplift the worries of many people by communicating well.
Simplification is hard work. It's an easy cop out to schedule an All Hands, share the changes, and dial off. But that's not effective. People absorb information at different paces and it's not thoughtful considering the caliber of importance.
I like being rewarded for bringing clarity and energy to people.
What’s your advice to someone getting started in enablement?
Have empathy towards your customer. Perspective is key. The reason your job exists is because there's a striving team who is trying to achieve higher standards and hit further milestones. You can imagine how hard they were working "pre-enablement" and now you're there to lift them higher, help them do more and be better, at scale.
What are you doing to develop yourself?
I learn a lot in conversations and relationships. I read the Sales Enablement community slack every day. I love learning from other people who are passionate about their profession. I feed off their energy and vibes. I also ping Whitney whenever I'm stuck, too and her enthusiasm for what she's doing is infectious and empowers me a lot.
Connect with Kaila on LinkedIn!