Interview with Danielle Wegenstein, Director of Marketing & Sales Operations, Sight Machine

7 min read

With an extensive background in customer success, Danielle Wegenstein is a sales operations leader who puts the customer at the heart of everything she does. I was keen to learn how Danielle uses her customer-centric experience to excel in sales operations and how she drives success in her current role as Director of Marketing and Sales at Sight Machine. We discussed the partnership between customer success and sales operations, the process of building out an SDR function, Sight Machine’s Tiered account process, managing the data trail between the marketing CRM and sales CRM, and more. After hearing about Danielle’s transition to sales ops, the interview began…

Rory Brown (RB): Can you tell us more about Danielle Wegenstein and your career to date?

Danielle Wegenstein (DW): I have been in tech for 13 years. My background has been a combination of customer success and operations.

When I first joined Sight Machine I worked on the customer side owning a few of our key accounts. At the beginning of 2018, I moved to more of an operationally focused role, doing sales ops, bridging the gap between Sales, Customer Success, Data and Marketing. And now I run Sales and Marketing Operations.

RB: I’m interested to hear more about your route from customer success into sales ops. Has your CS background helped you in your sales ops capacity?

DW: In order to be a strong Sales Ops leader you need to have a clear understanding of the customer.

With my experience in Customer Success, I was able to translate customer needs and priorities in helping to align our Sales Ops strategy within the organization.

Our customer success leads join the conversation early on in the sales process which helps with alignment and relationship building long-term. It is a true partnership.  

RB: How do you approach turning this qualitative data into points you can make decisions from?

DW: Sight Machine has a few buckets we review regularly and score on to prioritize inbound and outbound lead generation. We have ongoing conversations with our Customer Success and Sales team to understand customer needs, how the market is responding to collateral we distribute, which industries we should target and events we should attend, to name a few. These data points are what drive our sales strategy.

RB: You mentioned something there about action point and follow up. So let’s say you discover something from your crazy methods of collecting information that you think needs to be acted upon.

How does that whole mechanism work from discovery to telling the people what you have seen, and getting them to use it and then seeing if it has actually worked? The insight to action process.

DW: Typically, I float ideas by the various stakeholders, whether that’s over lunch, a coffee or grabbing five minutes when I see them walking around the office. Starting off with more of an informal conversation allows for honest, unstructured feedback. I can then take those learnings and start to build out a more formalized plan.

RB: What percentage of time would you say you are responding to requests (because we all know we are frequently asked for last minute reports and process changes etc) versus initiatives that are your own dreaming, coming up with something you have spotted pro-actively?

DW: Right now, I would probably say it is 85% requests or day-to-day work and 15% brainstorming.

RB: Focusing on that 15%, where do you start and how do you decide what to investigate?

DW: If I see an issue, or I see a place where I think we can work smarter versus harder, I take time researching, speaking to my network and brainstorming with co-workers. Using your network is key! This percentage of work is critical for all roles throughout an organization. You should always have the ability and time to think up new ideas or processes. We all need time to explore what we are passionate about in our day-to-day work.

RB: It would be good to understand one or two projects that you have been working on recently.

DW: At the beginning of the year, we brought on an SDR to build out our inside sales function. Part of the onboarding brought up the need for additional documentation and training. We’ve spent time since then building out a sales playbook and Sales and Marketing onboarding materials to help quickly ramp team members as we continue to scale. This process gave us a chance to step back and re-evaluate how the sales functions were collaborating, where the handoffs would happen, how we as a team better qualify leads and present new opportunities. It was a great point for the team to set a strong strategy as we moved into the new year.

RB: Let’s dive into that. You have obviously gone from salespeople doing the full cycle to taking a percentage of that cycle away from them and giving it to someone else.  How do you decide first of all what proportion an SDR is going to take and how do you justify that?

DW: It was a process we started last summer, by assessing how we generate and capture new leads. Initially, as a smaller team, the sales organization had visibility into the entire lead generation process. Building out our demand generation infrastructure gave us the ability to score and regulate new leads. This mechanism provided an instance funnel for our SDR team and a way for them to prospect new opportunities. This instantly freed up their time to focus on more strategic accounts.

RB: What is the argument for controlling the quality of leads that you are giving to the salespeople, versus enabling them to see everything?

DW: What has happened is a cultural shift in the way we manage and own leads. As a simple example, I have setup a few different lead views in Salesforce, giving each seller the ability to view their owned account leads and potential prospect account leads daily. These easy wins in process and time efficiency help build trust with the sales individuals, which is necessary as a sales ops leader.   

RB: So for all the leads that are left, how do you decide when sales should act on a lead versus marketing still has some work to do to get them ready for sales?

DW: We have many mechanisms to help with nurturing leads throughout their lifecycle, but two important processes is our scoring ladder and Tiered account approach.

Scoring leads is based on a handful of criteria, such as, title, industry and how many times the individual downloads content. Our SDR team views these reports daily and once a lead hits a certain score or threshold we move them to MQL in the conversation funnel, giving our SDR team instance access to prospecting the new lead.

Second, we assess our tagged Tiers twice a year to make sure they are aligned with our evolving sales strategy. This is something I highly recommend to organizations. Tiering your accounts, especially those which are strategic in nature is important and valuable for the overall organization.

RB: I notice on your LinkedIn you mention the acronym SLA which presumably means between marketing and sales. It would be great to hear more about the work you’ve done on that front. What does a sales SLA look like and conversely, what does it look like on the marketing side?

DW: We have stringent rules around how long a lead can be an MQL versus SAL or SQL and rules on when and how they should be converted to a contact. You need to have these rules and automation in place in order to keep the “engine” running and allowing for new MQL’s to surface. It is worth noting that having a qualification framework for the SDR and sales team brings alignment and framework to their day-to-day. 

RB: You are bridging sales and marketing operations. When it comes to the data trail between the marketing CRM and sales CRM, how do you decide at what point the data overlaps and appears in both, and then which datapoints appear only in each of those?

DW: That is a great question. A good example of what is captured in our Marketing CRM versus the Sales CRM is all the email content and nurturing tracks. This is specific to the Marketing CRM and not necessary from a visibility standpoint in Salesforce. What is captured in our Sales CRM is the campaign level detail, allowing the salesperson to see which campaigns an individual lead or contact has gone through.

RB: Let’s say we’re looking at reporting across the funnel, from marketing through to sales, where do you start in terms of getting a handle on what that flow looks like, and working out which bits are most important?

DW: At a basic level you need to start with the company website and other tools being used for new direct or indirect lead generation. This is where the top of the funnel starts and from there you can follow the flow through to closing a deal. For a new sales ops leader, it’s incredibly important to understand the levers in an organization’s lead gen program. Knowing these drivers will assist in how you prioritize your program development.

RB: How does you measure success in sales operations?

DW: That is a great question. There are a couple key metrics which any organization will benefit from, pipeline forecast, open opportunities, win rate, Sales vs Marketing lead generation, and number of prospect meetings per quarter or month, depending on how you measure your SDR team.

RB: Do you have common metrics and KPIs for the entire sales and marketing organization?

DW: Yes, we have some overlapping KPI’s, which helps with alignment.

RB: Great. Thank you very much for your time. 

Want to get more insights from sales ops leaders? Check out our other posts in the sales ops interview series.

At Kluster, we’re big fans of sales operations…

We recognise the growing importance of sales operations. No longer seen as the function that provides spreadsheets, sales operations is integral to building a repeatable, scalable sales machine.

That’s why we built Kluster. We make analytics and forecasting systems for you so you can spend time doing what you do best: uncovering trends and delivering growth defining insights.

Kluster gives you total visibility into the effectiveness of your sales machine and helps you generate credible forecasts to revenue leaders and the board.

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