From recruitment to sales ops, Rebecca Silverstein discovered a passion for tech, optimisation and working smarter, and did what she could to turn that passion into her dream job. Having joined Smartling as an SDR, she’s now running her own team as Manager of Sales Operations. I was keen to find out more about her journey. We discussed where to focus first in a new sales ops role, how Rebecca has built out a sales tech stack and how to create a successful onboarding process. After hearing about Rebecca’s transition into sales operations, the interview began…
Rory Brown (RB): Can you tell us about Rebecca Silverstein and your career to date?
Rebecca Silverstein (RS): I studied Finance at college and upon finishing my degree, started a career in recruiting. It wasn’t something anyone saw coming (including myself!) and eventually I realised it wasn’t where my interests lay. During my time as a recruiter, I spoke to a lot of people in tech companies, which sparked my interest in that area.
I had seen lots of transitions from recruitment into sales development, so I started applying for business development and sales development representative positions at tech companies to get a foot in the door.
That is how I started at Smartling and during my first year there, I discovered a passion for optimisation and working smarter, and I would take on additional projects to gain more experience.
During that time, I worked on a project for the Sales Director that involved scaling outbound email campaigns for the sales team. After that, I transferred to sales operations.
My first year in sales operations involved a lot of self-learning – teaching myself Salesforce, creating reports for the sales team and taking on the administration of some of our tools. My role started to expand when our current VP of Sales joined Smartling at the beginning of 2018. He had experience in running a sales operations team, so we were able to ramp up our efforts by re-tooling the entire sales tech stack and creating new processes. At that time, I also got my Salesforce Administrator certification.
In July, I was promoted to manage the Sales Operations team, which at the time was myself and one other individual. I now administer the CRM for the whole organisation, own the tooling and process for the sales team, and manage our team of (now) three.
RB: Perfect. That’s a nice place to start the interview. You are just over two years into sales ops now. What do you know now that you wish you had known when you first started?
RS: One thing I have learnt is that people aren’t always going to ask for things because they don’t know what to ask for. A lot of the value that I’m trying to deliver is finding things that other people might not be thinking about, or listening to what people are saying and trying to pull out what is important.
Another thing that I wish I had known is that more often than not, others are dealing with the same or similar issues that I am. I have made connections and formed a network with people in sales operations across different companies of a similar size, and it seems like a lot of the challenges that I thought were unique to Smartling are not and I’ve learnt that there is a lot of value in speaking with people who have done similar things before and discussing ideas for improvement.
RB: That is really good. Let’s focus in on your initial learning of finding additional value that people aren’t thinking about. Where does one begin with that? How do you identify an area, let’s say of the sales funnel, where you might want to create additional value?
RS: It’s natural for people to become very focused on their teams and specifically the people that report to them. But with a broader scope and understanding those metrics, there is opportunity to look outside and investigate what might be causing this or how it compares to other teams in the business.
RB: Have you mastered a tactful way of presenting insights that could put a sales leader and their team in a bad light?
RS: It’s always challenging to deliver feedback and potentially bad news. But what I have learnt, and am still working on, is to frame it as “This is where we are at; we are all on the same page here and we might have an opportunity to improve.” It’s more tactful than pointing the finger and blaming. Having a solution, or at least the ability to spark a conversation framed around what the end result is, can result in a more positive conversation.
RB: You were in the position of being the first sales operations leader at Smartling. What drove the need for a sales operations function and what was the first thing that that function tackled in the business? I think there are a lot of people reading our resources who are in that position.
RS: For me, the initial move was driven by that scale and outreach initiative I had taken on.
In terms of where to start first, from my experience as an SDR, I knew the biggest blocker in the SDR workflow was we were spending a lot of time researching better accounts to work.
That was something I had personal experience with, so I focused on that first. I think it’s important to start by focusing on something you already have experience of or you know is a problem, and get some quick wins. That will then immediately prove your value to the team and other stakeholders.
RB: So your experience as an SDR naturally led you to start with that issue. Were there any thoughts about the commercial impact or numbers that might be impacted if you were to fix this issue? Or was it more of a theory you wanted to test?
RS: I initially sent out a survey to the SDRs to get an understanding of what they were spending the most time on, with the idea that if we could eliminate time on non-essential activities, we could then re-allocate that time for more outreach.
So, everything else being equal, the theory was that we would be able to increase the amount of outreach by X number of hours that we gave back by eliminating some research time.
RB: Yes, fantastic. Moving onto the topic of technology. It would be interesting to understand what your current tech stack looks like and how it improves the efficiency of your sales funnel, from the moment an SDR picks up an inbound lead or creates an outbound lead right through to close.
RS: I will choose a couple of tools to focus on. Several years ago, we implemented Chorus, which is a conversation intelligence platform. It enables reps to focus on taking their calls and then be able to look back, comment and share key moments and insights from those calls, and solicit coaching from management.
So that is something that is both a tool and a process update that we made.
And then the other tool I’d like to mention is Salesloft. We implemented this a year ago for the sales development team and we have since seen 5X, 10X in activity across the team.
RB: Brilliant. Let’s take a deeper look at Salesloft. How did you arrive at the point where you knew you needed to invest in technology, rather than make better use of what you already had? How did that decision come about?
RS: Our VP of Sales came from an organisation that saw success with an outbound cadencing tool. When he started we were keen to channel that success and alleviate some of the SDR team’s manual efforts, namely spending a lot of time keeping track of who they are reaching out to. Our hypothesis was that this tool would help organise their days better, whilst keeping them focused and accountable on their activities.
We leveraged our network with other organisations and concluded that there are just a handful of players in this space that sit in this category. Those are the tools we focused on evaluating.
RB: How do you identify areas that you need to invest in and bring new technology to?
RS: In the past, we identified the key categories in which a tool or a vendor would be able to free up time for the team. Sometimes there is an event that brings one of these categories to our attention and then we get a conversation going with the team, asking how much time they spend on X and assessing whether there is a better way to get the task done. I take calls with vendors in various spaces to understand what is available, who the leaders are, and generally keep an eye on what is new to the market.
RB: So for you it is all about enabling people, freeing them up to do what they do.
RS: Yes exactly, that’s a huge part of it.
RB: Nice. It would be great to talk about the rolling out of new technology. If we start from the very beginning from getting people bought-in to the fact that we are about to invest in something new, all the way through to making it stick during the onboarding process.
RS: One of our more successful rollouts was Salesloft so I’ll use this example.
We chose Salesloft as a vendor particularly because we saw them as a great opportunity for partnership. Our sales rep flew in from Atlanta to New York for three days to sit with our Sales Development Team and answer any questions that they had. This was a huge help, particularly for those who were not going to be in the tool every day. He was able to help with the implementation greatly, and we also really tried to drive home how much this tool would help them hit their quotas.
It’s important that they understand the benefit and why we are spending time on certain things and not others.
RB: There’s often a lot to think about when you set up a new tool in terms of syncing it with Salesforce, new workflows etc.
How do you approach that?
RS: Simple is best, but at the same time I try to have everything as built out and robust as possible for the initial rollout, so that there aren’t a lot of updates I need to make and communicate to the team over time. Going back to Salesloft, we had an idea of what we wanted to use it for and I consulted with the implementation team there to understand best practices and ask questions, and then I tried to make my best judgement as to how this would fit into our process.
Again, in the interest of not having to constantly send updates to your team, I recommend trying to have it as prepared as possible for the initial rollout.
RB: Presumably, if you spot something you think needs improving or technology, your first port of call would be to talk to the person you report into, the VP of Sales in your case?
RS: Yes, exactly.
RB: Then when it comes to actually finding the right vendors, I presume that is then your duty?
RS: Yes. Sometimes people come to me with recommendations, or there might be SDRs reaching out to different people, so I will instruct someone on my team (more often than not, me) to take a call with them. And then we would go through their feedback and make a decision based on what is unique to each vendor and their pricing. Then I would have a conversation with my manager, the VP of sales and come to a consensus.
RB: You obviously speak to a lot of different vendors. In your experience, what makes a good vendor to partner with?
RS: Some of the commonalities that I have found to be most important to me are whether they are going to be a partner who is easy to work with, who will be able to answer questions, and be able to speak to specific issues. Are they there to support us when we have a question? Are they able to easily resolve things? Can the tool do what they said it would do?
RB: Would you say you might sacrifice shiny gadgets or functionality for the one that is more likely to make it a more pleasant seamless experience?
RS: We think about our non-negotiables. And if they check those boxes, then it would probably be deciding between who we believe has a better roadmap and would be a more successful partner long term. But if they are not ticking the basic boxes, regardless of whether they have the nicest team in the world, it is probably not going to be a good fit.
RB: That is a good point. What advice do you have for new sales ops leaders who have been given the responsibility to find new technology and vendors. How should they approach that?
RS: First of all, you should consider at a really high-level what you need this tool to do. And then from there, breaking it down and saying, so that means that we definitely need X, we definitely need Y, we definitely need Z. And then look at the features and benefits on G2Crowd or similar rating providers. But keep in mind you don’t want to just see the Best of the Best, you just need the best fit for you.
Then it’s about going through your criteria checklist and looking at all the vendors who have met that criteria.
RB: How would you describe the relationship between a sales ops leader and sales leader, how they depend and rely on each other?
RS: I think that the more aligned you are, the more effective you can be. Having an understanding that we are looking to achieve the same thing – more revenue – and really focusing on what is going to have the biggest impact on that is really important. It’s also important to understand their role and their point of view– for example, at the end of the year, the sales leader will likely be on closing out deals. And it’s probably not the best time to talk about purchasing a new tool.
And then also asking how you can help. As opposed to, “Here are all the things I want to do”, the conversation should be, “What is the biggest problem that you think we should tackle?” Alignment is really important.
RB: I like that a lot. The next question is an interesting one, and I’ve had quite a few different answers on this. How do we measure success in a sales ops role or team? What have you experienced there?
RS: I would love to hear what other people answer for this, because everyone I speak with says we are very metrics driven, but oftentimes it is very difficult to quantify sales operations performance.
So I would say that what we try to do is divide things into projects using OKRs: This is our objective, this is what the result looks like and these are the things that we need to do to get there in this time period. I know that some people also use a form of NPS score to understand if their work is actually making an impact on the team. It’s always good to ask whether the work we do is helpful and what we could have done better.
RB: I like that a lot.