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Sales Enablement PRO Awards 2022: Maximizing Rep Productivity at DailyPay

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Congratulations to Sales Enablement PRO Award winner Amanda Romeo and the DailyPay team. Learn more about the Sales Productivity award winning initiative below.

Sydney Lee: I’m excited to announce the winner of the 2022 Sales Enablement PRO Member Award for business impact on sales productivity. Congratulations to Amanda Romeo and the DailyPay team. I’m excited to be here with Amanda today, as she shares how her team built an enablement function from the ground up, that substantially increased productivity at DailyPay.

Amanda, I’d love for you to introduce yourself, your role and your organization.

Amanda Romeo: Thank you, Sydney. My name is Amanda Romeo and I’m the Senior Manager of Revenue Enablement at DailyPay. DailyPay, if you haven’t heard of it, is the recognized gold standard in on-demand pay and I spent my career in sales, operations, training and enablement, frequently building programming and enablement infrastructure from the ground up. 

SL: Absolutely, that’s fantastic and thank you again for being here with me today. I’d love to get started on the topic of your team’s efforts at the organization. To start off, how did you structure and scale your enablement program to train and develop your teams for success?

AR: Our revenue enablement programs are structured to support the different milestones of our revenue team members in the most scalable way possible. Our flagship program, which is called go-to-market summit, is a comprehensive onboarding program that is designed to train all revenue team members on how to quickly be productive in their new roles, assimilating them seamlessly into our culture, methodology and industry.

SL: Absolutely, that’s fantastic. I’d also love to know, what enablement initiative was most impactful to the success and sales productivity at your organization this past year, and how has DailyPay continued to foster a culture of learning through this initiative.

AR: Absolutely. Go-to-market summit is broken into various segments to support the stages in the new hire life cycle. In terms of sales productivity, our account executive trail, which refers to the programming dedicated to ramping our sales team, has been most impactful. With constant curriculum help assessments we look at this program on a quarterly basis, to make sure it keeps up with the fast pace of our company and our industry. This agile approach allows us to constantly move the line at how we enable our sales reps to produce quickly, which shortens the time to first and second sale dramatically, quarter over quarter. Second to our account executive trail is our sales support coaching program, which allows new hires to see one-on-one coaching and training from our training team on practical application of training concepts in actual deals that they are working on.

SL: To go forth on that, what was the biggest challenge your team faced and how did you overcome it?

AR: Speed to productivity is such a focus in our organization. Like I said, the pace at which our company, our industry move, the team needs to be extraordinarily focused on attention to detail, so between the quarterly program analyses we always improve the content to make it relevant to each new cohort that joins our team.

SL: That’s great, I love that. What has been the impact of increasing sales productivity on organizational objectives?

AR: Our enablement team success is tied directly to business results, namely time to first and second sale of our sales team, so we connect our onboarding programs to this metric and map the correlation, in order to attach our enablement initiatives to productivity. Most notably, the results from our training programs consistently improve year over year. From 2019 to 2020 we saw a decrease in time to first sale by about eight percent. Moving into the first half of 2021, it dropped another thirty-four percent and in that second half we saw another forty-six percent drop. That’s about a sixty-seven percent decrease in time to first sale from 2019 to 2021. On a similar note, our certification score went up about fifteen percent from 2020 to 2022.

SL: How do you measure the effectiveness and success of your team’s enablement efforts?

AR: That’s a great question. We keep a close eye on collecting benchmark data. Without it, it’s extremely difficult to tie enablement initiatives to business results, which I’m confident that we drive. When I started at DailyPay in the beginning of 2021, one of my first priorities was to identify the benchmark data on time to first sale, so that we could track that from Day One. We’ve also used tactics such as satisfaction surveys, blind testing to assess the existing knowledge and create thoughtful programming based on that, rep certifications. I use the Kirkpatrick Model to track the levels of impact, which covers four different stages: satisfaction, learning, behavior and results.

SL: Absolutely, that’s fantastic. I’d also love to know how you foster a culture of learning in your team to enhance productivity.

AR: Culture of learning in our industry and company is non-negotiable. If our team is not willing to always learn and improve, they won’t be able to compete in our market. It’s our responsibility on the enablement team, to champion that culture and enable leaders to reinforce it. We regularly release ongoing learnings and weekly communications and provide reinforcement tools to our leaders, to make their jobs easier or as easy as possible, when talking about training in the one-on-one’s in team meetings.

SL: How do you align with organizational leaders and goals to maximize your team’s impact on sales productivity?

AR: We have an amazing sales leadership team that dedicates their time regularly to align on training enablement initiatives, as well as coaching and reinforcing key learnings from training. Without leadership buy-in most initiatives can be a waste in my opinion – which I know is controversial, but it takes a lot of time for enablement to prepare for these programs and if we only spend a few hours with the reps and then leadership never talks about it again or reinforces it, we won’t see the results. Period.

SL: Going into part three, I’d love to talk about key considerations for enablement productivity in 2022. First, I’d love to know, what was your teams biggest learning in the past year and how will this impact the team in 2022.

AR: Our sales team grew tremendously in 2021. We’ve had a few record-setting cohort sizes and with this explosive growth, the training needs to keep up. It’s imperative that we focus on easily accessible content, training and communications in 2022. Consistency really is key and when we provide resources to our sales team that allow them to align on messaging in a just-in-time manner, we can be in more places at once; so on-demand learning and leadership enablement will be a core focus for us this year.

 SL: For the last question, now that 2022 is in full swing, how are you planning for the upcoming year as we continue to face a mixture of virtual, in-person and hybrid work environments?

AR: That is a wonderful question, which I think many practitioners are out to solve for right now, and I wish I could share a silver bullet here. The truth is, each organization is facing this in a different manner, through company mandates, increase of remote workers, technical limitations, the list goes on and on. In the near term, most of our programming will remain virtual, due to our organization’s guidance, but we are excited that we’re in the process of opening a new office that will be equipped with tools to help support a hybrid learning environment; and even more so, we’re looking forward to hosting in-person events and trainings in the coming months, as it becomes safer to do so.

SL: Absolutely, I’m looking forward to those in-person events as well. That’s all the questions we have for today. Thank you so much, Amanda, for joining us and sharing your expertise. Congratulations again for being our 2022 Sales Enablement PRO Member Award winner.

AR: Thank you, Sydney.



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